Clothing The Solo


Clothing The Solo


Want to dress better? In this episode, Peter McGraw has a far-ranging conversation about fashion with Rachel Lefort, a stylist with more than 20 years of fashion experience. In a previous episode, The Solo’s Promise, Peter explores an alternative story structure to the Hero’s journey. The Virgin’s Promise is a good metaphor for the single person resisting human domestication, embracing solo living, and flourishing—hence the name, A Solo’s Promise.  An important part of this alternative structure is the protagonist begins to “dress the part” as he or she fulfill their promise. For example, Cinderella’s transformation begins to occur when she puts on the beautiful ball gown.

Recognizing one’s solo promise begins with an act of re-invention—a change in how you think of yourself, how you behave, and perhaps even how you dress. Creating a new look—changes to grooming and clothing—was a topic in Kevin 2.0 (Episode #42), where a divorced man getting back in the game after a twenty plus year marriage.

Rachel and Peter discuss why dressing well matters—for yourself and for others. In particular, they address how improving your wardrobe can help you accomplish your goals, and how dressing well can be fun. They tackle some of the common mistakes people make and the challenges of updating your wardrobe.

If you stick around for the bonus material, they talk about dressing during COVID. Rachel suggests starting your wardrobe edit. Get a fashionable friend or professional to help you to find clothes that you should lean into and the clothes that don’t look good on you—either you donate or get those clothes tailored. This process will help you identify some gaps, especially “the basics” that need to be filled in for when the pandemic ends.

Today’s episode of Solo is sponsored by Wrapture Masks. Since Peter recommends wearing protection during sex, he also recommends wrapping your face when you go out into the wild. And Wrapture has made the best non-medical grade mask money can buy. It’s antimicrobial, breathable & most importantly FULLY MACHINE WASHABLE, so you aren’t one and done. One mask lasts over 50 washes and I’ve been using for more than a month and it’s my go to mask. You can find them at wrapturemasks.com. Use promocode WRAPTURESOLO at checkout for a discount.

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Listen to Episode #44 here


Clothing The Solo

In this episode, I have a fun conversation with Rachel Lefort, a stylist with more than twenty years of fashion experience. You may be wondering why I would have an episode on clothes, especially nowadays, but let me make the case. In episode 25, I explored The Virgin’s Promise, an alternative story structure to the hero’s journey. Because The Virgin’s Promise is a good metaphor for the single-person resisting human domestication, embracing solo living and living a remarkable life, I have co-opted the story structure by calling The Solo’s Promise. An important part of the structure is the protagonist begins to “dress the part” as he or she fulfills their promise. For example, Cinderella in her transformation, it begins when she puts on this beautiful ball gown. I believe that recognizing your promise begins an act of re-invention. A change to how you think about yourself, your behavior, and perhaps even how you dress. I’m still working on this idea, but I believe it’s important.

Creating a new look and changes to grooming and clothing was a topic in an episode with Kevin Nalty, a divorced man getting back in the game after a twenty-plus year marriage. These changes are not just practical, they’re symbolic and important. In this episode, Rachel discusses why dressing well matters for yourself and for others. In particular, we talk about how improving your wardrobe can help you accomplish your goals and how dressing well can even become, dare I say, fun. We tackle some of the common mistakes people make and the challenges of updating a wardrobe. Above all, please wear clothes that fit people. If you stick around for the bonus material, we talk about dressing during the time of COVID.

Rachel suggests starting your wardrobe edit, getting a fashionable friend or a professional to help you find the clothes that you should lean into and the clothes that don’t look good on you. Either you donate those clothes or you get them tailored. This process will help you identify some gaps, especially the basics that you can fill for when the pandemic ends. This episode isn’t for everyone. Soon after taping it, I read the book Party of One: The Loners’ Manifesto by Anneli Rufus. Anneli makes the case the dressing well doesn’t matter that much to loners and I get it. In any case, I hope you enjoy the episode. Let’s get started.

Our guest is Rachel Lefort. She is a personal stylist with twenty years of experience in fashion. She studied Fashion in New York, London and Paris, and now resides in Denver, Colorado where she works for J.Hilburn, a custom clothes company for men and women. For years, she’s also done personal styling for both men and women, and she’s helped me vastly improve the way I dress. Welcome, Rachel.

Thank you for having me on.

I’m excited to do this. I want to start with a callback story to some early episodes of Solo. There’s a movie called Limitless with Bradley Cooper. Have you seen this movie?

I have not seen this movie. I need to see this.

It’s a good Bradley Cooper film.

Anything with Bradley Cooper.

What’s that man not good at? He’s got everything.

Now, we know he can sing.

In this movie, he’s a writer who’s a bit of a loser. He’s a smart guy but he drinks and procrastinates a little too much. The story is about him getting his hands on this genius drug called NZT. Essentially, you take this drug and you get to use your entire brain. You become a genius. In that movie, he takes this genius drug and the first thing he does is he tidies up his apartment. Any readers of Solo knows how much I like tidying up.

It changes everything.

It’s a little bit of a cheat code for getting things started, making a change in your life. Here it is, a genius tidies up. The next thing he does, and this comes up in one of the episodes called Dude, Get A Haircut, he goes to a fancy salon and he gets a haircut. We know Bradley Cooper has great hair. He walks out of there with this amazing hair. The next thing is he starts working out. Any readers of Solo knows how much I believe in health, eating right, fitness and so on. Rachel, guess what he does next?

I can only imagine. Does he go shopping?

He updates his wardrobe. There’s a scene of him getting fitted for a leather jacket. He goes from this schlubby guy to this very good-looking, put-together guy, especially the clothing. My argument is if the geniuses are doing it, if the people who take NZT are doing it, why shouldn’t us mere mortals?

Bradley Cooper is giving us very good advice. Those are all important things to step it up.

Let’s start this off. Why does dressing well matter? Why does a genius recognize its importance?

It changes your whole attitude and it changes how you do everything. How you put yourself together and walk out the door, it can change your day. It affects your confidence. You do a better job at whatever you do when you got it going on. When you look good and you know you look good, then you’ve got that spring in your step like, “Damn, I look good.”

There’s a tendency for people to think that you dress well for others and there’s truth to that. I agree with you. There’s this level of confidence when you feel comfortable in your clothing, when you know you look good. There’s a lack of confidence when the opposite is the case.

If you’re self-conscious about the way you look and you’re tugging, pulling and you don’t quite feel right, your clothes don’t fit well, you know you’re a wrinkled mess and you didn’t have time to press or whatever it may be. If you don’t even know why but you don’t feel right and what you’ve got on that day, it affects you.

I think that is true that when you feel good about yourself, it helps you become a better person. You move through the world with more aplomb. It’s easier to be a better person when you’re feeling better.

When you’re confident, you’re happier also, and then you’re doing a better job. It’s a compound effect. It all adds up.

My personal story with this as a professor, I dress up when I teach. You’d be amazed at how many professors don’t do it. I see it as putting on a costume of sorts that I transform myself from this regular, everyday person into someone who is about to put on a performance. I see it a little bit like theater. In the same way that you dress up as an actor, I dress up as a professor. It does because when I walk into the room, I feel more confident.

You feel ready because you put on the correct clothes for the job. It does something in your brain to make you feel ready. That’s proof. You’re presenting.

That’s the other thing. It does matter for other people. I talk to people, especially men. Women are a little better about understanding this than men, but a lot of men say, “It shouldn’t matter how I dress. I shouldn’t be judged by the fabric on my body. I should be judged by my expertise and my abilities to understand the material and to communicate it clearly as a professor. It shouldn’t matter what I wear.”

I’ve heard that from women too. Sometimes I do speaking engagements about dressing professionally, how to add style with your wardrobe. I’ve had women also tell me that it shouldn’t matter. Men and women have this argument and I think they’re right that it shouldn’t matter. It’s your inner beauty that counts.

If you say it shouldn’t matter, it matters.

Unfortunately, the fact is it matters and there are many studies about it that we’re judged so quickly, subconsciously. They say that within 7 or 3 seconds, somebody forms a judgment about you and they don’t even realize they’re doing it. You can be in denial and say, “I am who I am and it doesn’t matter.” What I say is that you’ve spent so much time and money on your education. You’ve got a Master’s or PhD. You keep going and you’ve put all this effort into honing your skills and becoming the amazing person you are but then you sell yourself short if you don’t look the part. You don’t have to look like the lawyer if you’re the lawyer or look like a professor stereotype. However, if you present yourself, then you’re more apt to have a conversation and then you can share what an incredible person you are.

What it does is it opens people up. It gives you the benefit of the doubt. They pay more attention. When I dress up, for the reader to get an idea of what it is, I will wear a suit or slacks and a sports jacket and a button-down, no tie with some dress shoes or upscale sneakers depending on how I want to make it look. These poor students have to look at my ugly mug for hours on end. I might as well give them the best visual that I can give.

I’m sure they appreciate that.

The other one is that it says to them, “I take this seriously. I care about this. This is important. It’s important enough for me to put together this outfit for it to be well-pressed, matched and fit well.” Not only does it convey the importance but then it also conveys a bit of my own confidence in this.

When they know you have confidence, they have confidence in you. I like that you dress it up and dress it down so you look polished but you also look approachable. You’re not wearing the tie so it’s a little bit more relaxed, but yet the sport coat or jacket steps up your level of authority in away. When you’re intentional about it, you can totally dress down the shoes as long as it looks cool and polish.

I’m not putting running sneakers on. We’ll get a little bit about having a look because that’s a useful thing. I’m not suggesting anyone should dress like me. That’s not what this is about. I don’t want to create a mini-me. I want to get your reaction to this idea that I’ve been fussing around with. There’s this level of, “I’m going to try to enhance my wardrobe because it’s going to help me move through the world with more confidence and more comfort.” Secondly, despite my protests that it shouldn’t matter, it’s going to help me achieve the goals that I want whether that be professional goals or personal goals.

Being treated in a positive, respectful, professional way, having my insides match my outside, to be appealing to someone if you’re dating, or even you’re telling others at a dinner party or something, “I respect you in this context. This is important and I recognize this. I know you put a lot of time into hosting this event. I’m going to put some time into appearing in a way that’s consistent with that.” The last idea, and this is when I don’t think people understand especially if you’re not you, Rachel, who has lots of experience with fashion is that fashion can be fun.

You’re preaching to the choir.

What it turned for me was when I said fashion is like art for your body.

Except it is not tattoos, but some people think it is.

It’s exchangeable art for your body.

[bctt tweet=”Learning what looks good on you is not an innate skill, but it can be learned.” via=”no”]

It’s not permanent and forever. You’re not painted on.

Maybe you could speak to that idea for a little bit because the average person thinks of clothing first is utilitarian. “I’m going to wear these clothes to keep me warm in the winter, cool in the summer and shaded from the sun.” That’s the first level. Most people never move beyond that very much.

They think, “I’ve got to wear something.” It doesn’t matter what.

That second level is this idea of like, “I’m going to do this better because it’s going to benefit me and it’s going to benefit other people who I care about.” This third level is straight-up fun. That’s where we’re talking fast.

This is the next level. It’s fun to point this out, to share the perspective that you can make it fun and why not make it fun because you got to do it. We already said you have to care so you might as well make it fun whether or not you like shopping and a lot of people hate shopping.

Why do people hate shopping so much?

Shopping is challenging. It’s hard to find the stuff that you need. A lot of people don’t even know what they need. They don’t know where to look. If you walk through a mall, even in a department store, there’s so much. How do you know what departments to go to? There are trends that come out on the runway, for example. Every season, it’s constant trends. Neon might be in. It’s overwhelming. It takes some of the fun out when it’s exhausting and overwhelming because you don’t know where to go or where to start. There’s the finding the stuff and then the trying on and knowing what to try on. You’ve got to try different sizes. There’s vanity sizing, especially in women’s but also in men’s.

What’s vanity sizing?

The vanity sizing is if I took someone’s measurements, perhaps that woman is a size six but when she goes shopping, she’s a size two. She feels great that she’s wearing a size two.

She should be wearing six. It’s not that they’re labeling a 6 to 2 so you feel good. She’ll choose the two.

That’s what it is.

You’re kidding me.

No. There’s no standard. In the fashion industry, the brands can put whatever size number they want on whatever measurement. It’s annoying. In some brands that I know, I might be this size but in other brands, I’m on that size. It’s a marketing thing. It hits the thing where you psychologically want to be the smaller size so you want to buy that brand where you feel like you are a smaller size if you feel good about that. It’s deceiving and frustrating. Everywhere you go, you have to take two sizes at least into the fitting room of every garment.

It’s overwhelming in terms of the number of choices. It’s obviously time-consuming. You’re giving an example of something that makes it unnecessarily time-consuming. We’re in a little bit of a digression here, but it’s a worthwhile one because we can help problem solve this. We’ll return and problem solves some of this once people know what it is that they should be looking for.

We’re going to get back to how it can be fun.

It’s overwhelming and too much time. One is that you have to confront your body in a way that a lot of people don’t want to confront it. Very few people, unfortunately, walk through the world going, “I like my body.” Isn’t that terrible that almost no one walks through life going, “I like my body, it’s a good body?” Clothes shopping forces you to confront the things that you don’t like.

You’re right, especially when there’s bad lighting.

As an aside, I was working on a project at one point. It never went anywhere about how poor the lighting is in dressing rooms. We don’t want overhead lighting. We want front lighting because front lighting is the most flattering lighting. That’s the lighting you have when you get photographed professionally, with filmmaking, video, and so on. We live in a world though of overhead lighting. It’s terrible. It forces you to confront your body. The other one is the average person never has given too much thought about what works for them. They have no training. Where do you learn?

What a good point you bring up. This is not an innate skill of learning what’s flattering for your physique and what looks good on you. It’s not about the size but there’s proportion as well.

Let’s talk about some of the typical problems you encounter because that’s what you’re headed to.

It’s different for men and for women. With men, there’s vanity sizing as well. There are a couple of things when I worked with a lady on her wardrobe edit.

What’s a wardrobe edit?

A wardrobe edit is when she would like help going through her closet to update and to look at what she already has and say, “Is this working? Is it not working? What should I get rid of? What should I get?” I asked, “Maybe we can rework this in a different way or we have it tailored. It works better or differently.” I make a shopping list as we go saying, “These trousers would be perfect with different heel height. You need a different shoe.” Something like that, for example. What I’ll ask her before we get started with the questionnaire is, “Are there parts of your figure that you want to deemphasize? Are there parts of your figure that you want to accentuate?” That way, I know what she likes and doesn’t like about her figure. Also I ask if she’s changing her figure like working out, trying to lose weight. A lot of women will like something about something. They didn’t know their whole body, but they’ll like something. Somebody might feel that she has great shoulders, great calves, ankles and want to accentuate. Maybe she wants to de-emphasize her hips. There’s a way to do that dressing with smoke and mirrors. We can play with that with proportions in darks and lights.

You have this question of, “What are your goals? What do you like about yourself? What do you don’t like? What are you working on?” You have some of that. An edit is a lot like editing a book. There might be things you cut from the existing wardrobe, “You have not worn this polyester blouse since 1979. It’s gone. We’re donating it.”

I think we’ve done this in your wardrobe.

We have done a wardrobe edit for me. It’s a difficult thing to do for people because they have to confront their bad choices. Their body might have changed like this thing doesn’t fit anymore. There’s this thing called loss aversion, which is the loss of throwing it away or donating it looms larger than the gain of the space in the closet and the mental clarity that you never have to wear it again. That’s why Marie Kondo uses her, “Does it spark joy?” Her spark joy standard is designed to focus you not on the loss of the thing, but on the beauty or the greatness of the thing.

A lot of people laugh about it and make fun of it or some people do, but it’s smart.

There are the things to cut and if you’re editing a book, you also need to add. You might say you need to write another paragraph here to explain this point, which is the thing of, “Pete, you could use a new pair of dark jeans.” For the audience, Rachel helps me accessorize better. Do you remember this?

Yes. I had to pull you out of your comfort zone.

Tell the story.

You very proudly told me because you’re very minimalist. Would you say that?

Yes, I would.

You only wear black accessories, black shoes, a black belt and that’s it. Don’t even show me anything else.

What is a natural alternative?

Brown. You are far from your comfort zone. Everyone is wearing yellow sneakers. “Pete, you need them with a matching belt. No, it’s brown.” Finally, after years of working together, I’ve talked you into buying a pair of brown shoes that are not super formal but they’re in between.

They’re brown Oxfords.

It’s stylish. They have this patina to the leather. We had to get the brown belt to match. You had to take it for a test drive. Do you remember what happened? I remember something.

I will tell you this. That pair of shoes get more compliments in any other pair of shoes that I own. This is illustrative. It’s good for people to hear this. You had to teach me which of my outfits work well with brown, black, and either brown or black. You have pushed me even further into what you call fashion-forward, and we’ll come back to that. The last thing is this revision process, “The sentences are good but it could be better. Let’s revise it.” That seems like what you’re saying is you can repurpose something. What’s an example of that with a female client you might have?

Let’s say there’s this skirt that she’s been wearing to work. It’s a little bit flowy and I’ve looked back at her questionnaire. In the questionnaire, I’ve also asked her questions about adjectives she wants next to her name that says, “What is the look you’re going for? What is the style you want? How do you want your colleagues, your customers, potential dates, your husband, or whomever to perceive you?”

I do have married readers. They come in two forms. The first one is they save a solo mentality. They don’t live with their husband or wife, or they do live together but they believe in not being merged as much is much more independent. I have married people because it’s like a single’s porn, imagining what life would be like on the other side.

If you’re married or single, you still need to take care of yourself. All your advice is relevant. Even if you’re happily married, living a normal married life, you still are an individual. You’ve got to tidy your place, get a haircut, go to the gym and dress well. Back to my wardrobe transition.

She has this flowy skirt and you asked her these adjectives.

She’s got these adjectives that she wants to look chic, professional, polished, and whatever words it is that maybe this flowy skirt doesn’t seem to match up with the love she’s going for. I might ask her, “How do you feel when you wear this skirt? I’m not sure that this skirt at the office is doing you justice for the direction you’re going. If you want to amp up your style and you want this look, let’s repurpose this for Saturdays at the Farmer’s Market.”

That’s very useful. Some of the clothes I had, I would repurpose for painting the house.

Especially with your old jeans.

These ‘90 style jeans are perfect for painting.

The shorts you won’t wear out of the house.

We’re going to get back to that too. You do this edit and so then you identify where are the gaps in this closet? You’re then looking to fill them in with clothing that accomplishes the goals of your client.

I keep a shopping list like groceries.

For men, do you find the process to be similar?

I do. When I do a wardrobe edit for men, it is similar. I start with a questionnaire and get to know about his work, “Are you a manager? Are you customer-facing? Tell me about your work.” We look in his wardrobe and I ask him, “What does he wear to work? What impression is he making or image that he’s conveying?” I look at his wardrobe of what he needs. Some guys are high-tech at a startup.

They have all hoodies in their closet.

Maybe you’re going to pitch and look for funding but don’t want to go too far with a full-on suit and tie because it doesn’t fit either. I might discuss with him, “How about we throw on a cool sport coat even over something casual with your denim?” There’s a way to do it.

You mentioned one problem which is people’s comfort or discomfort parts of their body. What are the problems that you see with people in their wardrobes?

Some people do get emotional, more women than men, about their body because you were absolutely right about that. Other issues are personal experience. Having somebody come over to your house and go in your closet is personal. You’re talking about even individually or you’re saying with my work.

Let’s talk more generally first because some readers, they’re not ready for a closet edit. They’re at a point where their fashion choices, clothing choices or wardrobe choices are not something they think about. They might’ve been on autopilot. They might be wearing the same type of clothes for the last twenty years without thinking about it. For some people, they’re ready to call you, have you come in, and do this but others don’t even know how far they could improve, how much better off they could be.

Baby steps are good to not feel totally overwhelmed. There are a lot of resources also to look into what to get and where to start. Even starting with new denim can make a big difference. Updating your jeans to something modern.

Jeans are our problem. Let’s say it.

They can be a big problem. Everything starts with the fit. It’s a problem if you wear your clothes way too big.

You call it shirt fat. We need to take care of that shirt fat. It’s fine though because the shirt fat is fine.

That’s not yours, it’s the shirt.

It’s a lot easier to get rid of shirt fat than it is to get rid of fat-fat.

The tailor is a quick fix that you can’t do at the gym so easily.

It took me many years to start wearing clothes that fit me. I’m long and lean. The problem is I have long arms. If I wanted to buy a shirt off the rack that the sleeves fit, I would buy an extra-large also because I’m a guy who grew up with Sylvester Stallone and Arnold Schwarzenegger films. That was, at a time, where big beefy guys would look versus nowadays which is muscular but lean, more of a classic, natural V-shape on a guy. I’d wear an extra-large because I didn’t want to be large, I wanted to be an extra-large. I would wear a shirt that fit in the sleeves, fit in the length but had this billowing under and then I’m going to tuck the shirt in.

Did you do the thing where you push it to the back?

I’ve probably done everything. I didn’t have these big muscular legs, but I would wear these pants. The problem was getting that to work. The problem is if you’re a thin guy, but you want to try to look bigger and you wear bigger clothes to look bigger, you look like a skinny guy in a tent. If you’re a bigger guy and you try to wear even bigger clothes to disguise the fact that you’re a bit overweight, you look like a big guy in a big tent. It’s unfortunate. A lot of people don’t wear clothes that fit. Part of the problem is clothes that don’t fit in the big size are still comfortable.

A lot of people prefer to dress for comfort. When they wear clothes that are so big, you look bigger than you are. Some people even want to hide their figure when they’re not confident in their bodies. They want to hide and cover it up. I have experienced helping somebody dress in something even it’s a little more tailored and more fitted, but not tight. There’s a difference. It just fits, it looks like the person lost weight. You can feel like you lost weight even though you haven’t by losing the clothing excess that you don’t need around your body, whether it’s a guy wearing. This huge billowy shirt and having the shirt fat shaved off or it’s a woman wearing some big tunic. Instead of putting on some great denim that’s fitted to her and a fitted blazer which looks amazing. Blazers are my favorite thing for women because they give her shape at the waist and sculpture, but they don’t cling like a cardigan. They stand away but still provide shape.

I like that idea. The tough thing about the clothing that fits is that there’s not an easy off the rack solution because off the rack clothing for me it’s small, medium, large, extra-large. The problem though is I’m a large in some ways, extra-large in others, a medium in other ways depending on what part of the body is connected to the clothing.

You always have to compromise off the rack.

The first solution is to find a good tailor.

That’s what I was going to say. Go to the tailor. When you shop, know that tailoring might be an added small expense to plan on because it will make the clothing that much better. If you find that $3,000 dress marked down to $10, you’re so psyched about, and it needs a little tweaking at the tailor, great. If it needs a whole new cut and reset the whole thing, if it needs too much tailoring, it’s not worth it. Keep in mind the amount of tailoring. A store associate, if you’re shopping in a store, they will be able to guide you in this. Some stores offer alterations also.

If I remember correctly, for a man’s shirt, let’s talk about some shirt fat. The key is making sure that the shirt fits off the rack in terms of the neck and then also the arm length ideally, but you can close the amount of fabric on the sleeve. It can be tightened down and then the fabric underneath the armpit and then the fabric around the waist.

If you put your arm out like that entire line from your wrist, your cuff, all the way down your armpit and down to the hem, all of that can be taken in.

If all of that is taken in, that might cost $30, $40. When I was a grad student, the idea of tailoring a shirt for $30 or $40.

It could be a lot. It depends on what you paid for the shirt.

You have to work a little harder on the time side of things in terms of finding better things that fit versus spending money.

It takes effort. You spend time on writing a paper, stuff for work, or whatever it may be. You might like to cook. You love shopping for your mountain bike equipment. You take the time to research and find the right stuff. You have to invest the time whether it’s online, receiving it, trying out at home, going to the tailor, returning what doesn’t work, or asking a friend who’s honest whether it’s shopping the store and talking to the sales associates or bringing a friend. You have to invest the time to hunt and gather.

I would argue that if you’re buying good quality clothes, an additional $30 or $40 to get it to fit well in order to be excited to wear it and to get the benefits of wearing clothing that pops and looks good on you. If you can make that work, it’s a worthwhile expense. It will spark joy. The next level is to see someone like you or to get custom clothing made. That’s with J.Hilburn. J.Hilburn, we’re looking for sponsors for Solo, so I hope you sponsor for us. A custom shirt would include someone like you measuring the guy’s body or girl’s body and then having the shirt custom made. My personal experience with you is it’s not that much more expensive than buying a shirt and having it tailored.

It sounds expensive, custom made, but it’s not as expensive as you might think. We do custom shirts now for $100. It’s not as expensive as some people think it must be at least $200 or something, but there’s a variety, there’s a range depending on your fabrics. There are sales of course.

I recognize I have readers who are 22 years old going to middle-aged folks to people who might be close to retirement where they’re not thinking that much about dressing for work or whatnot. They have a much more casual life. I look good at this funeral.

I do have a lot of guys that tell me they need to have that black suit just in case. I need you to have it in your wardrobe. That is sad to say but I was going to say, you should dress for your casual wardrobe as well. That’s just as important because you want to look good on the weekend, after work, on a date, or doing something with your friends. It’s not about dressing for work. I always encourage my clients to pay attention and we shop for casual stuff. With J.Hilburn, you can take the fit of your white clean button-down shirt from work and apply the same fit to your linen shirt for weekends, for the summer, or on top with your five pockets or whatever. You can change the styling up but it’s all about fit.

You’d be so proud of me. I had a pool day and I never would have done this years ago but I need to get another suit. I have this old-style blue bathing suit with white stitching. It’s a great suit. I love it. I wore a white polo shirt with it to match the stitching. I bought a new hat. It’s like a summer fedora.

We’ve been looking at these for years.

I found one and I bought it and then a pair of Wayfarer style sunglasses.

You must look so cool. Barefoot or shoes?

I was wearing flip flops because I was in a suit and stuff like that. I was at the pool, but I could imagine a more casual sneaker that I could probably have used for that. Normally, what I would have done with the pool is you put on a baseball cap on a T-shirt and then your bathing suit. You don’t even think about it because you’re going to the pool. There are people at that pool who you might want to see having seen you look good. We’ve talked about clothing that doesn’t fit. That’s the number one major problem that people have. I would say this if you tackled that problem, you fixed 50% of your problem.

At least much more than 50%. Fit is the most important part. Otherwise, it looks like you’re wearing somebody else’s clothes. Even if it’s beautiful and designer, fancy or you love the fabric, it doesn’t matter if it doesn’t fit.

What’s the next big one that you find in terms of wardrobe and clothing choices?

Some people don’t know how to put the outfit together and also how to accessorize. I guess that’s more dicing after but it’s sometimes where to start. When I do speaking engagements, I teach and I do more for women than for men, some mixed for companies. For women, I’ve done these seminars about how to build your professional wardrobe with style, for example. I always start with wardrobe basics. Basics are the black pants or the navy pants or whatever it may be. Where to invest? Where to save? What looks good? Creating these building blocks to then create your outfits around. The building blocks could be boring but then we add the fun afterward. I look at it as the basic things like the basic pants, basic blazer. Let’s say that these are the blank canvas and the accessories are the paint. The trendy stuff can also be with the accessories and the fun stuff.

It’s interesting to hear you say this and it goes something like this which is, there are these kinds of clothing for certain circumstances and for occasions. If you lack the clothing for that occasion, you either skip the occasion, which is unfortunate, or you wear something that’s not appropriate for the occasion. How do you show up and be confident? How do you show up and say to the people who are hosting the occasion or part of the occasion, “This is important to me?” Guys get into trouble with this a lot. There are guys who have clothing for work and they have clothing for tailgating but they don’t have clothing to go on a date or to go to a dinner party. They’re in this space that it’s not appropriate and it’s hard to feel good. What you’re saying are basics. You might need a professional sport jacket, but then you also might have a more casual sports jacket.

Something fun, and it depends on your personality too. The navy blazer but what about the fun like burgundy plaids work coat if that’s your personality. It’s got cool lining in it. It’s something to express your personality, something casual and for those occasions. As we already said, it takes time and effort, especially with custom clothes. You need to plan ahead and say, “I’m going to set myself up.” It takes a little extra planning because it takes time to order these things. They’re made just for you. It could take four weeks or so plus your fittings to make sure that the fit is correct or if we have to tweak it a little bit at the tailor, we will. Plan ahead and get the things that you want to set yourself up within your wardrobe. When those occasions come up, you’ve got it. You’re ready. You have the versatility that this blazer could work at this dinner party I’m going to, cocktail party or this swanky event downtown. It could work for a date night at the theater or it could work in different ways.

It does take a little bit of planning. One thing that people don’t recognize is it’s a lot of work but once you have the basics, especially if you do a good job getting stuff that works well for you and is good enough quality, it lasts for a while. It doesn’t have to be as much work after the initial fixed cost.

Especially when you determine the sizing. If you shop in J.Hilburn or any custom clothes, then you know your fit. Once you’re fitted, it’s much easier. You can even order custom clothes online which is cool. We do a Zoom session. Even shopping the stores, it’s an investment of time to figure out what works. When you have those basics and you get them in the better quality, this is where you invest. You invest in better quality because as you said, you don’t want to have to shop for new black pants every season if you’re one buying black pants.

I’m going to offer another one to get your reaction to it. We’ve already alluded to it a little bit which is, you’re wearing something terribly out-of-date. You might either be wearing something that is very clearly connected to a time period that has long passed. We already talked about baggy jeans that are clearly way out. They’re not as a bit out whether you’re wearing it or you’re 45 but you’re dressing like a twenty-year-old. That happens with men and women.

It does, like the miniskirts. You told me not to hold back. I saw many miniskirts on the runway, they’re one of the trends. They’re all over the stores. They’re looked so cute on the mannequins, and they look so cute on the 22-year-old who is home from college or just graduated from college. It doesn’t mean everybody should wear them even if you have great legs. Sometimes, it looks a little too young and it looks off.

I have my own pet peeve which is middle-aged men in their shorts. American middle-aged men wearing shorts, not at the gym, and not at the beach. The world does not want to see your pale, hairy, middle-age legs. The other one is flip flops at brunch.

People reading are probably like, “Why? What’s wrong with that?”

They’re comfortable. It’s hot out. I understand that. My joke is when the middle-aged man wears flip flops, he chooses his own comfort over the comfort of others. There’s a little bit of a transition where you don’t have the body you’re used to. You’re more established. You’re not a teen. This is a good segue. We can move on from problems. The fun thing about clothing is you can move away from your problems so far that you can start to have fun. That’s a nice thing. You’re no longer fleeing bad decisions and discomfort and so on. You’re now approaching excitement and fun. For example, dressing for the pool that day was not an anxiety-ridden set of decisions. It was fun and exciting choices.

That’s good. Once you figure it out, it’s fun.

It can be fun. You use this term fashion-forward. What is your definition of fashion-forward?

It’s like pushing the envelope a little bit and getting out of your comfort zone. It’s different for everyone but fashion-forward is also being a little trendier, not just being in classics that are timeless. There’s definitely a place for that. It’s pushing it to something that is a little more runway. Maybe it’s bolder colors, patterns, or something that’s high-fashion.

It’s something I won’t do yet which is I will not mix patterns.

Pete, I’ve seen you mix pattern.

Barely, but I liked my solids with one pattern.

It’s safer.

I grew up poor and I have these minimalist tendencies. I want to keep it simple. I want to remove as much decision making as possible. I want to know, “These pants we’ll go with these shirts and those pants we’ll go to those shirts. I can mix and match like Garanimals style.” People who remember those Garanimals style for kids.

I have a lot of guys who asked me to make Garanimals for them.

You pushed me to be a little fashion-forward and an example of this is I have this blue suit. It’s my favorite suit. It looks good to me. Let me add that some people don’t dress for their coloring.

That’s another thing I was going to say as well. You’re absolutely right.

Can you say more about that?

When you dress for your coloring, it’s about bringing out your features, your eyes, your hair, your face, because you don’t want someone noticing your outfit. You want them to notice you. If you were fair like light blonde hair, fair skin and you’re wearing all dark colors and somebody squints from far away, they’re only going to see your clothes coming. They’re not going to see your head. You want to wear something that flatters you, not to say you can’t wear black because black is universal and makes you feel good or whatever.

As a general rule for dressing, your most flattering colors is to go with something tonal with your hair and your eyes. Those are the first two rules that are simple to follow. If you have blue eyes, when you wear blue, it brings out your eyes. If you have gray hair and you look great in grays, you just do more than you would in brown, for example. There is also the value of your coloring. If you have pretty dark hair and dark skin, it’s easier to look good in bold, darker colors because you have more of a contrast or value contrast.

It’s a little bit beyond the scope of this conversation but I want to bring it only because of the details. Everybody looks different, but I have gray hair, pinkish skin, and blue eyes. Blues and grays work well for me.

That’s a no brainer. That makes it easy to dress for your hair and your eyes. We’ll keep it simple. I have an example I can share. One of my favorite colors has always been magenta, which is this dark, purply, pink color. I noticed from photographs of myself years ago, I look terrible in this color. My skin looks yellow. I don’t look good. I figured out what it was. It’s this color that makes me look washed out. It’s the wrong tone for my skin. That’s not something easy to identify. Now, I wear it elsewhere. I have a pair of shoes in that color that I love. The point is that if you take time, look in the mirror, hold up some different colors and feel prettier or more attractive in certain colors than others, then this can help you. Even if you don’t know why certain colors can wash you out.

We have to say this, I don’t expect anyone to do this on their own. You need to find friends who are going to be honest with you who have some taste and experience or you need a professional like you to help with it. In the same way that I don’t think people should change the oil in their car alone if they’re inexperienced. Lean on people who have expertise, comfort and who are going to act in your best interests.

Nobody knows that you had to get help. It’s your secret.

Until episode one of Solo where you’re a guest spill the beans and tell the world that you’ve had a stylist. This is about expertise in this idea of fashion-forward. I have an episode about what makes people cool. When you talk about fashion-forward, you’re talking about coolness. The idea is to push the envelope. You don’t want to push it so far that you’re deviant and people look at you sideways, but you push it a little bit just enough that you’re different.

You’re taking a fashion risk.

The example of this is the blue suit that we were talking about. You one day said to me, “You know what you could do with that suit, Pete?” This is after you helped me get the brown accessories. “You could get a gray belt and gray shoes and it’ll look good.” I was like, “Really?” “It’s fashion-forward but it would look good.” I remember I went out and bought this not super expensive stuff because I was like, “I don’t think I can invest in that.” I bought some Steve Madden shoes, gray shoes, gray belts, and so on. I worked at the airport one day and I had three people, including one of the TSA workers says, “You look good.” I remember I sent you a text message. You’re meeting with CEO or something and you showed the CEO the text.

I was at this fancy dinner with the CEO and a bunch of leaders at J.Hilburn and the CEO is standing next to me. I got a text from you. It said, “I’m at the airport. I got all these compliments wearing the clothes that you picked out for me.” I’m like, “Check this out.”

For a guy, it might be a little bit different kind of accessorizing or it might be a sport coat in a situation where most people are a little dressed down. When you talk about being fashion-forward with your female clients, what comes to mind as an equivalent story that might inspire our audience?

Trying a trend but again not every trend is worth trying, let me say that.

This is a few years old now. Suddenly out of nowhere, there were a bunch of women wearing long sleeve blouses with their shoulders exposed.

That’s called a cold shoulder.

For some women I was like, “That looks great. She’s got great shoulders.” I also remember thinking that’s a fad.

It is a fad.

It went away pretty quickly.

It was everywhere. That was a way to be a little bit fashion-forward. That’s an easy trend to wear.

What would be a more traditional fashion-forward hack that you would give a woman?

It could be something printed, something bright, something bold. It’s might be hot pink pants or something crazy like that. I remember years ago where the colored denim was the big thing, but it’s been a while. I have a friend in Denver who is very stylish and she posted a picture of herself in a pantsuit. It’s an off red and it looks gorgeous. That’s something high fashion than not everyone can pull off. It looked good.

That’s the thing is when you start getting into fashion-forward, there are not the basics. It depends on the person’s body type, the style that they’re developing or coloring and so on. That’s not a one-size-fits-all.

It may be some cool asymmetric thing and have a high slit on the dress or something, a little sexy and edgy.

The thing about it is that if you go that route, at first, you’re going to be a little uncomfortable. When I say uncomfortable, you’re going to feel a little bit uncomfortable in that look at first.

When you’re new to try something out of your comfort zone.

What happens is this. It’s those situations, no one ever compliments you for having the basics. If you do something a little out on your edge, and I talk about this as one of the principles of Solo is to live on your edge. You want to live on your edge where you’re not bored, but you’re also not totally stressed out. Being on your edge, I went to the airport, I was on my edge there with the gray accessories. When you live on your edge, that’s where you get the compliment. That’s where the remarkable stuff is happening.

It changes your courage the next time.

It does. It emboldens you to do it again and to keep trying that. Let’s get back to the problem of shopping. Let’s finish up with some solutions.

Solutions are helpful to hear.

We talked about your choices are overwhelming. It feels like a waste of time. You have to confront your weaknesses and you often don’t have the expertise. There’s a lot of uncertainty there.

Number one is finding someone to help you. For you with J.Hilburn, it’s part of the service. I come over, get you fitted, talk about the fit you want and help you pick out the clothes. It’s all part of the service of getting you the clothes. You pay for the clothes, but I also consult for you. Helping with shopping, that’s one way to go. Another way is if you go shopping at the stores, working with the sales associates that are there already. If you can build a relationship with somebody in the store that you like, that’s helpful. You can then just call that person, “I need this. Can you set up a fitting room full of stuff to make my life easier?” That’s what they’re there for. You don’t have to pay for that.

There’s a tendency for people to avoid these associates because they feel uncomfortable asking these questions and so on. It’s important to recognize that’s what they’re there for. They want to help. The good ones want to help because they’d rather help than stand around.

They have a lot to offer but maybe they won’t click with everyone and they’re not all as knowledgeable as the next person. It depends.

In the same way, you want to find the right fit with the clothing, with the person helping.

Also, bring a friend. The other thing is to bring a water bottle, snacks for yourself like a child. If they say, “I need to parent myself here because this stinks.” When you go jeans shopping, it’s like swimsuits, you’re going to try on a million and lock yourself in that fitting room until you find one good pair that works.

My personal story getting started with this is in my early 30s. In my late 20s, I started to improve my wardrobe. One was a girlfriend who helped me who was very fashionable and wasn’t afraid to criticize. That helped me get rid of some of the bad stuff like pleated pants, braided belts, tucking polo shirts in, and stuff like that. The next level was I had a very good friend who when I was doing my post-doc and she would visit, I called it, let’s go to the big tree. We would walk to downtown Princeton. We would go to Banana Republic, J.Crew and one other store. We would look to see what was in the clearance racks, what was on sale and what was in there. She would advise me about what would work, what wouldn’t work and would tell me what would fit. I remember her saying to me, “Pete, you have to stop wearing clothes that are 1 or 2 sizes too big. You have to stop doing this.”

It’s a good thing she pointed that out. Many people have no idea they’re doing that.

I agree with you having a friend do it. There are these other options. There is some personal shopping. Sometimes, Nordstrom will offer this where you give them your sizes and they have it waiting for you. There are things like Trunk Club nowadays, and other versions of this that will send you clothing and you can try it on in the privacy of your own home.

You send back what doesn’t work.

These are all imperfect, but they do solve some of the problems that people have.

It takes a few go-rounds at least to receive the things you like and it’s still an effort because then you still have to ship stuff back and try it on. As you said, there are benefits of all these different things and remember, it takes effort. You have to put in the effort.

The issue is it’s hard to get around. You’re either going to have to throw time or money at this problem. It’s a little bit of a matter of understanding where you are with your financial situation or where you are with your time situation and how much you want to be able to invest in this. You can go crazy and spend thousands and thousands of dollars. I would argue that you don’t have to spend that much to make wild improvements.

With me, if somebody hires me, that’s an investment to pay for the service but I shop everywhere and anywhere. We could spend all our time at T.J.Maxx or Nordstrom. It doesn’t matter. I’ll look for quality and I’ll look for fit. It takes a little longer to hunt and gather, but it doesn’t matter where we shop. The point that you can save money for sure and also by making the right decisions and not buying the wrong thing or not buying the same thing again and again, always going back to it and still not feeling great about it.

You should be excited to be wearing the clothes that you’re wearing.

You should be and if you feel like you’re always stuck in the same thing or you can’t get out of this pattern of what you’re wearing all the time and gravitating the same thing, then get some help from somebody who can help change your perspective whether it’s a stylist or a friend.

Depending on your budget, where you’re at, and so on. I would say start slow, start making the improvements, and then you can build on these things. I recognize a lot of people are completely overwhelmed reading.

We should get some tips as advice.

Let’s finish with some tips. What I’d like to do, we’ll come back if people want to stick around for the bonus material. I want to talk briefly about COVID. Dressing during a pandemic. What are some tips that you want to leave the readers with?

Make a shopping list. Look at your wardrobe and think about how you want to look. What are some adjectives? If you call someone and your name is on caller ID at their house or their office, what do you want them to think about you? I want to look professional, cool, or whatever it may be, and then go through your wardrobe and think about, “Do I look good? Does this fit? Do I look professional?” Think about those adjectives. Does this look cool?” You can have a friend come over and do that. Make your shopping list on your own as you do this.

I love these jeans, but do they fit? Not really. They don’t fit anymore so put on the list that you need new jeans. You keep going with shoes and with everything. On your shopping list, you can prioritize a few things that you need. Think about your work right now. What do you need for your work? Generally, what can you prioritize? There are many sales right now, think, “I’m going to prioritize new jeans.” Look at three places or even start with one place like a department store that has several brands and orders a few pairs of jeans. It might be in the next size if your old jeans don’t fit. Try them on at home, go through that process, and like, “I found some great jeans.” Check the box.

You could do that with a couple of categories. Take baby steps. You don’t need to push yourself out of your comfort zone yet. You don’t need to take fashion risks yet or add all the fluff and fun until you feel like your clothes fit or with what you have. If you feel like these dress shirts that I have, you’re a guy, I love these shirts, but they are a little billowy or my neck is big, I had to go up in size but they’re too big around my waist. You work out and you have the V or you’ve got long arms like you. “I’m going to take these to a tailor and have them fitted.” That’s a great place to start because you’ll feel like, “My clothes fit so much better and I didn’t have to spend a fortune or a ton of time.”

It’s important if you can lean on folks, friends, or professionals for advice and encouragement. It takes a bit of a village.

It sounds counterintuitive but it’s a way you could save money.

That’s a great starting point. Rachel, thank you so much for doing this. I hope it’s helpful for people. It’s good to get people to start thinking a little bit. The world would be a better place if more people are dressed well. A little bit throwback about doing it.

I like how you said that. I agree. It feels good when you feel confident. It’s all about confidence.

I thank you for doing this. I thank you for helping me look better.

It’s my pleasure. Thank you for your trust. Thank you for having me on the show. What an honor.

It was great fun. We’re going to talk from the bonus material about COVID but until then, cheers.

Thanks, Pete.

We’re back with a little bit of bonus material. I’m going to keep this short because Rachel and I have a tendency to talk and talk. I want to talk about COVID dressing. There are three things that are happening as I think about it. The first one is people are wearing pajamas all the time. I get that sense. The second one is they don’t have opportunities to be out in public, to be social, and to wear their full wardrobe. The last one is mask. People are wearing masks. What have been your thoughts about those topics or anything else that’s come up during pandemic as people are quarantine, isolating, social distancing and so on?

Let’s talk about video conferencing because a lot of people are video conferencing from home right now. They are dressing from the waist up, which makes sense. There’s a new term called your Zoom shirts.

I’ve heard about this where people have a shirt on a hanger and they put it on before Zoom call.

Throw that sport coat on but keep your gym shorts on the bottom, which is what a lot of people are doing. Pajamas on the bottom and your button-down on top, your blouse, or whatever. My warning is that if you’re on this video conference and you have to get up for something, you could be busted. You might want to throw on even if it’s a pair of jeans, throw something on the bottom that’s not your pajamas or cover your boxers or something.

The choice of that Zoom shirt matters like getting a good pattern, no pattern or solid probably works better than a pattern because of the camera.

You don’t want it too tiny of a pattern. It could be a bigger pattern.

The other one is getting their lighting right. You want to be front-lit rather than top lit.

The other thing is the position of your computer camera. The lighting is huge. If you have a window and you can put some a table in front of the window so you’re looking at the light, then the light is on you and your camera sees the light on you, but then lift your computer up off the table. Put a box under it or anything.

It should be a little above eye level, looking down a tiny bit.

Not too high up so it’s looking way down on your forehead or your cleavage and not too low so somebody seeing your nose hairs either.

What else comes to mind in terms of COVID for you?

The masks you brought up, that’s a thing. That’s definitely a thing.

It can be potentially a fashion statement.

It’s a new accessory, love it or hate it. You could wear a medical one that you throw away and that’s fine. It doesn’t have to match but if you want to wear a fabric one and you want to make a statement or you want it to coordinate, then go for it. It is another opportunity.

I’ve talked about sponsorship from J.Hilburn. Solo has a sponsor and it’s Wrapture Masks. If you go to WraptureMasks.com, they have a black mask and now they have a new white mask both looked very sharp. They’re 100% machine washable, anti-microbial, and you can use promo code, Wrapture Solo, for a discount. I’ll put a picture in the exhibits here. I wore that same hat that I told you about earlier with the mask and a black polo. I look pretty good in it. It’s a decent look.

You wore the black mask.

I have an idea. I want to get your opinion about it. I get it especially if people read this episode and they go, “That’s all nice but I’m not going to be dressing up for a long time.” I see it as an opportunity. You have to be home a lot more than you would be otherwise right now. What a perfect time for a closet audit?

It’s the perfect time.

What a perfect time to start identifying the things that need to go the holes and then now, because of mail, you can start to do wardroby-type stuff. You don’t have to go to a store as much but getting started in terms of cleaning out your closet is a good first step to use during this time.

I’ve done some Zoom or video sessions too. You definitely can even on your own. You have more time to schedule a few hours and go clean out your closet. I’m hearing it to comment on what you said that there’s not a ton of opportunities to wear what you’re wanting to wear. That once things changed and we can get back to life, people are going to want to dress up. What do you think?

It will be refreshing to go out especially if you’ve been taking care of yourself. I know a lot of people who have got fit during the quarantine. They get to show off this new body with the potentially new look.

In the meantime, you have a little bit of in-person work, socially distanced drink with a friend or whatever. You can wear a few things. Otherwise, hold onto it if you love it and it’s something in your wardrobe that you feel good in.

The idea is think of this as prep time. You have a little extra prep time that you wouldn’t have otherwise.

It’s like life has a pause that you can catch up.

You have to put a lot of things on hold but that’s the first step of identifying those needs.

You have to prep wardrobe. It’s a good opportunity.

The other one is we got to go outside, get some fresh air, some sun, and go for a walk. Why not look nice for your walk? That’s being outside and that’s being social now.

It goes back to that conversation of dressing well casually and paying attention to the casual wardrobe. It’s not just about work.

Anything else that comes to mind in terms of thinking about quarantine life and dressing and so on.

It’s good to be comfortable but at the same time, when you are getting ready for a work call to remember that when you dress for what you’re about to do, it changes something. As you said in our episode, Pete, about getting ready to go teach. You find the outfit that’s like a costume, even though it’s not a costume and it prepares you mentally for what you’re about to do. It’s the same thing with getting on a work call. You’re preparing yourself. You could show up even if it’s not video, you could show up in your pajamas or sweatpants, but something changes mentally when you dress. You don’t have to wear a full suit and tie. When you put on some work-appropriate clothes, you sit differently, act differently or something in your brain. It shows up differently.

If everyone else is mailing it in you, you get a chance to stand out.

When you’re face-to-face and you can show that, but even internally. There’s a study called Enclothed Cognition. I don’t need to dive too deep in it but it’s interesting. You can chime in if we’re not out of time.

Essentially, it has this idea of how you behave and how you get treated change based upon. They used people wearing lab coats as the stimuli on that.

The artist’s smock versus the medical lab coat.

They had these very substantial effects on the participants. Folks, let’s hope we don’t have to do many more COVID-related topics but I’m afraid we’re going to be in this for a little while longer. The one good news is you have a little extra time if you get committed to making some of these improvements. Rachel, again, you’re great. I appreciate your time.

Thank you so much. This has been so much fun.

It’s my pleasure. Cheers.


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About Rachel Lefort

Rachel LefortRachel Lefort is a personal stylist with 20 years of experience in fashion. She has studied fashion in New York, London, and Paris – and now resides in Denver Colorado. She works with J Hillburn, a custom clothes company for men.


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