in: Outfit Guide, Podcast, Style

• Last updated: July 2, 2023

Podcast #282: How a Man Develops His Sense of Style

You’ve probably encountered a man who has an impeccable sense of style. The way he presents himself —  down to the smallest details — creates an impression that seems confident, but not fastidious. How does a man develop this type of a style sense? Is it something innate or something acquired through lots of trial and error? 

My guest today explores those questions in his book, Men and Style: Essays, Interviews and Considerations. His name is David Coggins, and he’s written for Esquire, The Financial Times, and Traveler. In Men and Style, he interviews some of the biggest tastemakers in menswear today to figure out the alchemy of the sartorial arts. Today on the show, David and I discuss how a man’s father leaves a lasting influence on his taste in clothing, the style mistakes even the most dapper of grown men made as teenagers, and how the goal of style isn’t to religiously follow rules, but rather to feel comfortable in your own skin.

Even if you’ve never thought much about how you dress, this is a fun podcast. And it’s your chance to hear about the goofy clothes I wore in high school. 

Show Highlights

  • Why David decided to write a style book of tastemaker interviews rather than a how-to
  • How fathers influence the style of their kids — especially as they become adults
  • Where tastemaking men in the world of style got their taste from
  • The lasting impact of men’s magazines like GQ, Playboy, and Esquire
  • The age at which one defines their style
  • How your style changes as you get older and the phases of style one goes through
  • Garish mistakes that even style experts have made
  • Combining style, authenticity, and presentation
  • Reasons to dress better than you probably do right now
  • What David wears at home, and how what he wears impacts his mindset
  • Why dressing like Don Draper is bad idea
  • Addressing young men’s complaints about “dad style” and looking too old
  • How women like to see men dress
  • Items that every guy needs in his wardrobe
  • Where can men express their style besides clothing?

Resources/People/Articles Mentioned in Podcast

Men and style book cover david coggins.

Connect With David Coggins

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David on Twitter

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Read the Transcript

Brett McKay: Welcome to another edition of the Art of Manliness podcast. You’ve probably encountered a man who has an impeccable sense of style, the way he presents himself down to the smallest details creates an impression that seems confident, but not fastidious.

How does a man develop this kind of style? Is it something innate, or something acquired through lots of trial and error? My guest, Dave, explores those questions in his latest book, Men and Style: Essays, Interviews, and Considerations. His name is David Coggins. He’s written for Esquire, the Financial Times, and Traveler Magazine among many.

In Men and Style, he interviews some of the biggest taste makers in menswear today to figure out the alchemy of the sartorial arts. Today on the show, David and I discuss how a man’s father leaves a lasting impression on his tastes in clothing, the style mistakes even the most dapper of grown men made as teenagers, and how the goal of style isn’t to religiously follow rules, but rather to feel comfortable in your own skin.

Even if you never thought much about how you dress, this is a fun podcast. It’s your chance to hear about the goofy clothes that I wore in high school. After the show’s over, check out the show notes at David Coggins, welcome to the show.

David Coggins: Thanks. Good to be here, Brett.

Brett McKay: All right. You got a great book out. It’s called Men and Style: Essays, Interviews, and Considerations. We’ll get more into the book in a little bit. Before we do, for our listeners who aren’t familiar with your work, can you give us a little bit about your background?

David Coggins: Yeah, of course. I grew up in Minneapolis. I’m a Midwesterner, but I’ve lived in New York for about 20 years now. I’ve written about art. For many years, just about art, for Art in America and other magazines. Then I started to pulled back and wrote about things that interested me like fly fishing, and design, and tailoring, and wine, and travel. That’s mostly what I do now.

I’m a contributing editor at Conde Nast Traveler. I write for Esquire and other places and this is my first book. It was an exciting project to do.

Brett McKay: Yeah, what was the impetus behind the book? Why did you decide to write this book? It’s a style book, but instead of the how to on style, or how a suit should fit, how a cuff should break on your pant. It was just that you interviewed a bunch of taste makers in the worlds of men’s style. What was the inspiration behind that?

David Coggins: That’s a very good way to describe it. For one thing, I was having, not a crisis, but I was about to turn 40. I thought I’d like to have a book. I looked back at the people I knew and cared about and things that had mattered to me.

I thought about dressing and lessons we know about style, not as, like you said, what to wear to a black tie event, but how clothes express ourselves and the men who I admire, who I think dress well, how they have a sense of who they are and how they fit into the world. I think that happens as you get older and you start to look at your father and realize the way he was as a man. Just like you said, I started to talk to people who I thought were interesting. A lot of them are friends of mine.

I said, “How did your father dress? How did you dress as a boy? How did you arrive at where you are in the world?” It was really incredible to hear these stories from really hot shot guys talking about bad decisions they made, the same bad decisions we all make, or have made, what we wore to prom and other disasters, bad tattoos, and mustaches, and things like that and how we arrived at the world view we have now. Clothes were just a way to express that, but a very powerful way.

Brett McKay: Yeah, who were some of these taste makers, these guys you interviewed?

David Coggins: I think people you’d know like Whit Stillman, the film director, Sid Mashburn has a got a great story, Gay Talese, Jay McInerney, the writer, a lot of editors and writers in New York like Nick Sullivan at Esquire, Michael Hainey, Jay Fielden, who at the time was editor at Town and Country. Now he’s the editor at Esquire, Aaron Levine who works at Abercrombie and Fitch now, my friend Michael Williams. You know a lot of these people. I think they were really … Of course, they’re friends, but they were really honest, which I liked.

They didn’t know what anyone else was going to say. Sometimes when you talk to people they want to just, “I only buy denim from this place in Japan. You got to know somebody.” It wasn’t like that at all. They were very frank and really honest and humane. I think one of the things that I like about the book was that people really opened up. You felt closer to them because of it.

Brett McKay: Let’s talk about some of these mistakes that these guys made along the way.

David Coggins: Yeah.

Brett McKay: Let’s not talk about the mistakes first. Let’s talk about dads. That was one of my favorite sections about how these guys’ dads influenced their style. It’s weird. I’m 30, almost. I’m 34. I find myself dressing like my dad. My dad, which is weird. When you’re a teenager, you think, “I’m never going to do that.” Little subtle things, that’s what my dad did. How did the fathers of the men you interviewed influence their style?

David Coggins: That’s a really good thing to bring up. One thing that was cool is that the men all came from different backgrounds. Some of their fathers were really dapper. Some were working men. I think there’s a time that you listen to your dad when you’re really young. He’s the first man in your life. Then there’s a time when you go against what he says just because he’s your dad and you’re 13 and you can’t tell what makes sense and what doesn’t.

I think the interesting part is what you’re describing is that you bend back to the smart things he said as you get older and then you can see more clearly. I think the effects on people are very strong. Sometimes you don’t see them until you’re older.

One cool thing in the book is that I asked people for photos of their dads when their fathers were young, when they were in their 20’s and 30’s. That’s really probably the best part of the book, to see all these great guys from all over the world. Some of them dressed up and some of them dressed down. You really get a sense of who they are. That was nice.

I think when you see your dad, you’re a kid, you just see him as your dad. As you get older, you see him as a man and the kind of decisions he’s made. You see him in a broader view, in a way that his life that didn’t have something to do with you. Before, you see him through the filter of just his responsibilities towards you. I think when you get older, you have a little bit better perspective on that.

Brett McKay: How did your dad influence your style?

David Coggins: My dad, I’m very close to him. I still am. I just traveled with him to Europe. Very strongly. He influenced it. His name is David as well. He’s an artist, and set designer, and a writer. He wanted me to dress, I guess you’d say appropriately. I couldn’t wear a tee shirt. I had to wear a collared shirt. There were definitely rules. It was very important that I would know those rules before I broke them.

I guess people would probably say I dress a little formally, more formally than other people. Now that I’m older, he thinks I’m too conservative, that I’m always wearing a tie. He dresses more casually than I do. Since he’s a big guy, he wears more bold colors and patterns that I don’t quite do.

It’s funny to see how that changes. Sometimes you learn something from you dad. You take it too far maybe. Maybe I did take it a little too far. I do like to wear a sport coat and a tie most days.

Brett McKay: It’s a good look.

David Coggins: Thanks. Sometimes, though you do it when you aren’t made to do it either. I think some people, you ask what people learn from their dad. I think some people react against that. Some people … It really depends on your relationship. I’m always fascinated by people who clearly share a lot in common with their parents and those who don’t.

Brett McKay: Yeah. Besides dads, where did a lot of these men get their style influence when they were trying to figure it out?

David Coggins: That’s really interesting too. In some cases, you have people who are from far away from big cities. They really had to study hard. That’s been true for 80 years. Whether you’re talking about Fred Astaire and Cole Porter, people who are from the Midwest who worked really hard and came to New York and invented themselves, as opposed to people from London and New York, who grew up going to Paul Stuart Store and were very urbane from an early age.

One thing that’s interesting, to me, is how these men, mostly who do live in New York, and London, and bigger cities now, how they arrived at that. It’s not just their fathers. At that time, many of them, magazines were a big part in their lives. In a way, that’s hard to imagine now, Esquire, and GQ. This is before the Internet, really. People reading those things and Playboy, for that matter, as well, and how a magazine had a lot more cultural impact than I think they do now.

You have Instagram, and Street Style sites, and a million other things. I also think that magazines viewed their mission differently then. They really thought that they were an arbiter of taste and took that seriously. I miss those days personally.

Brett McKay: Yeah. When you were interviewing these guys, did any common style icons pop up over, and over again?

David Coggins: The first thing I should say, something they had in common is that when were boys, everybody had very strong opinions. That was something that I learned. When they were seven, or that they liked a color a lot, or they didn’t like stripes, or they would make their mom go back to buy a different shirt, because they didn’t like the one she got.

She got them a sweater that someone begged for and then he refused to wear it. It was very interesting to see how these strong opinions, even before you know you have opinions, there were strong beliefs that these boys had, which was very interesting to me. Then, I think that teenage life is so interesting. In some cases, you have uniforms at the school you go to.

There were British guys in the book. They very much had … It was interesting to hear just how intense and finely regulated those uniforms were. I think some people, if they said they didn’t like it at the time, but in retrospect, it meant they didn’t have to make these intense decisions. Clothing decisions when you’re 14 and 15 seem like such monumental things.

I think at that time, too, you’re trying to express who you are and you don’t quite have it down yet. Maybe you want something with a big logo, or a sports jersey, or something like that. Once you get out of the heat of the moment those don’t always look so good in the aftermath.

Brett McKay: Yeah. No, yeah. Let’s talk about that. When did a lot of these guys establish their signature style? You just said here that some of these guys, when they were seven, they were very opinionated about their clothes. I wasn’t at all. If my mom bought me Bugle Boy from JC Penney, that’s what I wore.

David Coggins: You weren’t so difficult as some of these guys.

Brett McKay: A lot of these guys, you can look at them, that’s like that’s Nick Wooster, that’s his style. Look at Mike Williams. He’s got his thing. When did a lot of guys, when did they establish that? Was it in high school? Was it in college? Was it later in adulthood?

David Coggins: I think it’s later. That’s a really good question. It’s a really basic thing. Something that I think as you … One thing I like about the way men dress is a well dressed man, he knows something about himself. I think dressing well is about self-knowledge. When you see that, that doesn’t mean you have to wear an Italian suit. It can mean you wear the right jeans and tee shirt, but it looks like you know who you are and how you fit into the world.

I think that almost by definition has to happen as you get older, probably on the far side of 30. It means you’ve had a few jobs and you know where you live. The same way your apartment, or your house starts to come together at a certain point, your wardrobe does too. I think that just in general, probably, right around where you are, 34 is a good time. You’re a little more settled in what you want to do. You know what you need and how to communicate it.

To be honest, you have enough money maybe to get the things that you want and even to know what you don’t need anymore. You’ve gone through some phases. You’re like, “We can put to bed some of these experiments.” I think having those phases is natural, though. You don’t just come into the world perfectly formed. If you did, that would almost be unnatural.

Brett McKay: Yeah. What were some of these phases that people went through?

David Coggins: It was funny to me to hear guys that they were particularly obsessed with more, not even street style, just really garish Abercrombie and Fitch things, or more hiphop clothes, that sort of thing that people have in college that you don’t really know that they have if you’ve met them much later.

Michael Williams was in a more hiphop zone when he went to college. That’s perfectly understandable. I was totally shocking to me even though he’s a good friend of mine. Somebody like Jay McInerney who’s a little bit older, he totally embraced the shoulder pads era in the ’80’s. I don’t think anybody looks back on that look fondly, least of all Jay.

He was very kind to let us use what his author photo from that era. It’s like probably a fancy Georgio Armani double breasted suit that just three people could fit into it. It’s enormous.

Brett McKay: That’s funny. Yeah, when I was in high school, I was in the punk ska, surfer. I went through that phase. I was in high school when the whole swing revival happened, Rudy Vallee. Me and my best bud, we’d wear these dark denim jeans with these silk bowling shirts. As you look back, we look back, it’s like, “Boy, God. We looked hideous.” It was just absolute terrible.

David Coggins: It was so understandable though. I love that. I think when you’re younger too, you look for tribes, or groups to be a part of, whether it’s a band that you really like, or an era. That’s totally natural to do. You almost have to live through it in the moment. If somebody told you, “Maybe that silk shirt, a little bit too blousy.” You’re like, “No, it’s perfect. I tracked it down. It took me two months to find it. I can’t wait.” It’s probably good. Not that the Internet didn’t exist when I was 18, or 20, because some of those things are better left in the past.

Brett McKay: Yeah, I feel bad for teenagers these days. Everything’s documented. There’s no room for experimentation. It’ll haunt you the rest of your life.

David Coggins: Absolutely.

Brett McKay: Did you go through any weird phases growing up?

David Coggins: It’s funny I have to say I didn’t go through crazy phases. I once had a goatee for a little while. That is not doing anybody any favors. I had long sideburns from an early age that I don’t really mind that I did that. I think I didn’t even really know what I was doing. I just had them all of a sudden. I think when you look back at something like that, it’s the earnestness in your approach that is a little shocking.

It’s like you seem to take, at least when I look back at myself, I took those things so seriously. I believed in them so completely. I don’t think you have the kind of self awareness that you have as you get older. You think whatever band you’re into is the greatest band ever. Whatever you’re wearing is really important to you. You even believe in the ad campaign and all the things that go around it.

You don’t have the kind of reflection you have when you’re older and you can pick and choose a little bit more deliberately. When I look at myself then, I see somebody who was … I was very much into art and writing, and literature, but really liked the idea of being an art student. My version of what that looked like was maybe influenced by the movie Some Kind of Wonderful, which was a really good movie in the 80’s with Eric Stoltz as an art student, not surprisingly. You’re just not fully formed as yourself yet. I think that’s why it looks like the clothes are wearing you. You’re not wearing the clothes.

Brett McKay: Let’s talk about style in general. A common theme throughout the book was this idea of authenticity. Authenticity seems like it’s an existential goal. Everything has to be authentic. Style is a lot about a performance of an image you want to put out to the world. Can not be authentic, because you’re trying to convey something that maybe is not true to you, but you want others to think of you. Is it possible to be both stylish and authentic? If so, any notable stylish men who have combined the two?

David Coggins: That’s a great question. I think there’s always going to be some friction. How you dress is definitely a presentation. I don’t know if that makes it unnatural, but it’s definitely you’re presenting something to the world. I like that. When I see somebody who is very well dressed, I feel reassurance from him. I think he’s doing something. He’s showing the world that he wants the world to be a little bit more formal, or a little bit of a better place.

You can get carried away with that. I like to see a man who’s dressed well on an airplane. I feel like he’s trying to lighten the mood a little bit. At the same time, I think a well dressed man does it for himself, as well. You have this balance, something for the public, and for the people you see, and even respect, and to formality, and a certain amount of good manners.

Also, the pleasure someone gets out of clothing that they care about. That involves a certain type of secret pleasure that I think most well dressed men have. When I see somebody like Gay Talese, who’s a legendary figure, doesn’t need me to tell him he’s well dressed. I can see that he does it partly because of the way he views New York and social life here and also, legitimate pleasure he gets from tailored clothing and traditional clothes made well.

Almost everything he has, there are details that nobody would know about beside him. At the same time, when he walks into a room, you certainly recognize it. That’s a good example of somebody who has it both ways. I think, most people, when they look at him would say, “He’s got an authentic sense of who he is.” I think that’s a good thing.

Of course, something like that, you can’t just try to be authentic. In many cases, it’s what you arrive at over time. I think that is really one of the themes of the book and really one of the themes of the things that I care about is when you know what is enough.

If you think about any place you care about, or any artwork you love, whoever’s made it, or whoever is behind it knows when enough is enough. When they want to do something more, and that’s a little more flamboyant and it feels right, or when they know when to keep something simple and they know that that’s right. I think that that is really a goal that we all should have, but of course, you can’t pursue it. It has to come to you.

Brett McKay: Yeah, because once you do that hard pursuit, the clothes start wearing you, instead of you wearing the clothes.

David Coggins: Exactly.

Brett McKay: You can always tell he’s uncomfortable.

David Coggins: The sense of comfort is huge. I think the one thing that makes me a little bit sad is that, for a variety of reasons, men in America have a resistance toward suits, and sport coats, and formality, partly because they had a bad experiences when they were young. Then they associate it with conformity, or businesses, or wearing them against their will.

That’s really too bad, because suits can be very comfortable. They can be very expressive and very personal. Most men look really good in them if they’re good, if you go get a bad one, of course it’s not going to be a nice experience. There’s no reason that a man shouldn’t have a good suit and look terrific in it.

Brett McKay: Yeah, I love that point you made earlier about dressing up to bring a little bit formal — Dressing up for others, because you want to make others feel good. I notice that too. When people dress for the occasion, it makes the occasion feel … I don’t know. It has more heft to it. I feel like that’s something we’ve lost with our very casual culture here in the states.

David Coggins: That’s a really good point. It’s a funny thing, because people respond when you dress up. If you show up and see your girlfriend and you’re dressed well, she’s going to like it. There’s very few men, I know, whose wives, or girlfriends don’t like it when they dress up. Beside the people who are close to you in your life, just in general, if you’re in a restaurant and you see somebody who’s ready to be there, it’s really nice.

I think I always like to go to see what people are wearing at the opera in New York. That’s a very international crowd and to see what people’s versions of the best thing in their wardrobe is usually pretty funny. It’s also sweet and reassuring and nice to see people, even men … There’s a group of people who get together and they just all wear a tuxedos. It’s like that’s fantastic.

I think somehow we’ve gotten to a place where we view dressing down as some … Authentic is the word used before. It’s like there’s not artifice in it. That works if you own Facebook, dress however you want. If you don’t you do not look good in a hooded sweatshirt. Don’t wear one to a meeting, or even out of the house.

Brett McKay: Do you work from home?

David Coggins: I do.

Brett McKay: Do you dress up at home?

David Coggins: I do. I dress up. I don’t wear a sport coat in the house. I just feel more pulled together if I have a collared shirt and a big sweater that I like to write in. It’s definitely what I wear inside. I guess it would be in the Mr. Rogers vibe. I absolutely like to feel pulled together. I just feel more alert that way. Yeah, I think that’s a good way to say it.

Brett McKay: Yeah. Here’s another thing I’ve noticed too, since we publish style content on our site. I find a lot of the style content that we put on the site, it’s geared more towards 30 year olds, 40 year old guys. I always get pushback from even guys who are in their late 20’s, 30’s, 40’s that the idea of style we’re promoting is too old. It makes everyone looks like dads like it’s a bad thing to look older and mature. Have you seen that as well?

David Coggins: That’s an interesting point. I think the issue is when you see these clothes … First of all, I love the way old men dress. I have no problem with that. My dream style is an old Italian uncle. When I go to Italy, or when I look at style sites, I like to see what older Italian men wear. They have this sense of formality and a sense of self expression. Italian tailors are fantastic. They really look terrific.

I think when you talk about complaints that people have, or pushback, they’re not seeing how the clothes change when they wear them. I think that there’s a real issue with editorial in magazines and online. It’s like dress like Don Draper. That’s a terrible idea. Don Draper looks great. The show’s taking place in the ’60’s. Jon Hamm is super human. The clothes are made to flatter him and the era that he’s in.

You need to know what makes sense for you. How are you built? What’s your coloration? How big is your head? What color is your beard? Then you say, “Having a narrow lapel, super small collar, really tight tie makes your head look big and it looks silly like you just wanted to dress like someone you saw in Mad Men.”

I think people have to start with who they are and what they need and then work from there. That’s something that I think partly because of the way clothes are sold, we have brands that have very strong sensibilities, so they can communicate to people what they believe in. I’m not sure that’s a really good thing.

If you went back 50 years, or a little bit more, Brooks Brothers, or even a proper tailor is really trying to find what makes sense for you. I think when people start with that, they’re not going to look old in a suit. They’re not going to even look old in a cardigan if they bring some energy to it and things fit correctly and the color’s right. They’ll look really alive and they’ll be surprised at how good they look.

They have to give themselves a chance too. I think when people wear something the first time, I have complete belief that wear it around your house by yourself. If you wear something, people shouldn’t know it’s new. It should look like you’ve had it for a long time. You shouldn’t look like you’re trying to decide if you like it or not.

If I get something crazy, I’ll keep it in my closet for a year. When I’m ready, I’ll wear it out. I’ll even just wear it around the house to break it in.

Fred Astaire threw his suits against the wall to take the newness out them. I think once something looks like it’s yours, it’ll look good.

Brett McKay: You also interviewed some women to get their take on the way, what they like to see on men. Any insights there for guys, or were the tastes so varied that there isn’t really good advice there?

David Coggins: The basic insight is one we all know, which is that women are smarter than men and that was amazing to talk to. The women I talked to were writers and creative types and incredibly smart. It was interesting to talk to them, because it was about their relationships with men and the clothes that men have.

I think they like people dressed up. They like men also to be masculine and manly. I think that, at least the people I talked to, and then I would say the women I know in general, find it not effeminate in any way, but very masculine if a man is comfortable dressing up, or even comfortable wearing pink. That’s something that they find attractive. I think that’s true. I don’t know if that was a surprise. It was nice to have it confirmed.

I think that men don’t like it when they feel like they’re being dictated to. That was a reminder there as well. They don’t want something to be forced down them, whether it’s by a store, or their girlfriend, or whomever else. Sometimes you have to let the man feel like he made the discovery himself, that he came to it himself. He’ll think it’s okay.

If somebody’s stressing on, “You’ve got to wear more color. You should really wear this.” he’s going to resist. Some things men just don’t grow out of. That type of resistance is one of them, I think.

Brett McKay: Yeah. Like we said earlier, there isn’t a lot of prescriptive advice on style in the book, which one thing is I loved. It was refreshing to see that in a style book. I’m curious. Do you think there are items that every guy should have in his wardrobe?

David Coggins: Absolutely. I’ve been asked this since the book came out. People want to know what do I think, where do you start? It’s hard, of course. My basic rule is if Fred Astaire wore it in a film, it’s probably a good idea. If you go back and look at Fred Astaire’s style, he wore classics, gray flannel suit, blue blazer, oxford shirts, white bucks. He looked terrific.

I think even if you don’t wear a suit a lot, you should have a good suit. When you wear it, it’s almost always going to be an important situation. You should be comfortable in it. People don’t look at it that way. They say, “I only wear this once a year, so it’s not a priority for me.”

I would look at it the exact opposite way. I think a good gray suit, or a good blue suit that you’re comfortable in, at a place that seems to understand you, is a good thing to have. An unstructured sport coat, I think, is a really good thing to have too. A lot of companies are making them now. It’s something you can wear with jeans. You can wear it with trousers. I think it looks really good.

I think a man should get one of the classic things, like a good English brogue. If you have the staples in your wardrobe, you’ll wear them more than you think. I don’t think you need a lot of clothes. I would get, usually, the best version of something you can afford. Try to wear it a lot. I think you’ll be happy you have it.

If you really want to get specific, I also think knit ties look really good on men. You don’t have to think about pattern, but the texture’s really nice. You’ve got some color in there. I don’t think men take advantage enough of texture and color. I think they get overwhelmed with concerns of pattern. I think that can be distracting. I wear very simple pattern clothes myself for the most part. I take a lot of advantage of texture and color.

Brett McKay: Going back to Fred Astaire, that guy work a cravat sometimes.

David Coggins: Cravat. If you can dance like Fred Astaire, you can wear a cravat. That is a little bit dandy-ish. People who are going to wear it probably even have one, or know they’re going to wear it. You got to draw a line somewhere. I think, in general, sorry to cut you off, is that you want to stay within a comfort zone. You can push it slightly. I have a velvet coat. I never thought I would have one. Now I’m used to it. I love it. The cravat is definitely a step that most men are going to find uncomfortable.

Brett McKay: Do you know any modern guys who can pull off the cravat?

David Coggins: I think I do, but they’re really in a rarefied group of people. The thing that I like about really successful dandies is that they make what they’re doing seem natural, even when it’s very rarefied. I know some people who’ve worn some very, very extreme clothing. When they do it, it seems completely natural.

Even Nick Wooster, one the keys to his success and something I really admire about him is he makes most of what he wears seem like completely understandable and how you see the world the way he sees it. When you have that confidence, that’s a really good thing.

I also think people will go a lot further with you than you think. If you wear a hat that’s a little daring, the first time your friends give you a hard time, the second time, they’re used to it, the third time, they think it’s your signature style. You’re described as the guy with the cool hat. When you want to wear something enough to make it yours, once it becomes yours, that’s a very strong place to be.

Brett McKay: Besides clothing, where else can men express their sense of style?

David Coggins: That is a great question. It’s funny though, if you see a man that you think is well dressed, you think he’s going to be good at some other things too. A lot of men I like, they’re good cooks, not in necessarily a flamboyant way. They’re capable in the kitchen. They’re well read. They like to travel and travel a certain way. You’d take their advice about places to visit.

I think these are the things that just happen as you get older. If you’re curious, or like to interact with the world in a certain way, it’s no surprise that you know about those things. The book is not trying to get men to dress like me. I’m happy to look different than other people.

I think it’s men to dress like who they are and maybe a slightly better version of who they are. I think you want to ask a little bit more of yourself, especially as you get older and hopefully have more success and are more secure in where you are in the world.

I think once you have that, then a certain amount of sense of who you are, that will go into other places too, how your home is decorated, the way you travel, how you entertain when you have people over. I think all of those are an expression of who you are and the things you care about. I respond to all of those things when they’re done well by other people.

Brett McKay: One of my favorite sections in the book was talking about things that guys collected, or what they collect.

David Coggins: Absolutely.

Brett McKay: Sometimes it was just really weird, some of the stuff. It made sense when you read what their other insights were about style. That weird thing they collect is, “Yeah, that makes sense that he would do that.”

David Coggins: It’s funny you say that. There’s a part in the book too about what are things you’ve inherited from your father, or grandfather. In some cases, it’s quite obvious why something was passed down. It’s a very nice watch, or it was dog tags from somebody who was in the war.

Other times, it isn’t obvious why that thing was passed down, but you could tell that it’s important to the person. There’s a history behind it, whether it’s just a western shirt, or a Stetson hat. I like these things that has meaning that people give to them over time, whether it’s a collection, or something that’s been inherited.

I think that’s appealing to me. I’m not as interested in things that someone, a marketer is trying to tell you they have meaning because there’s a logo on it, or it’s really expensive, or a capsule collection, or a collaboration, or a hard to get, or there’s a line out the store. Those things will come and go. The things that your father gave you, or that you’ve collected because you have an affinity towards whatever the thing is, that’s more meaningful.

I think we should look for the meaning we give to things, not the meaning that magazines, or marketers give things. That’s hopefully a lesson people will take from the book.

Brett McKay: David, this has been a great conversation. Where can people learn more about your work and the book?

David Coggins: I actually got a web site for this book. It was funny. When you get to a point where you … It seems like everything has come and gone and we learn in different ways. At one point, everybody had a web site; then nobody did. If you go to, you can read part of the book.

I’m on Instagram. I love Instagram. That’s also davidrcoggins. If you Google me, I don’t know. I’ve got articles everywhere, probably too much for people to read about.

One thing, though that’s coming out that people might be interested in is in the March issue of Conde Nast Traveler, I went on a road trip through the Scottish highlands on our way, with my friend, Matt, and my friend, Jake to the Harris, where Harris tweed is made. That was a really cool trip and a really fun thing to do.

Talking about traditional ways of doing things, Harris tweed, which has been made in very specific ways for hundreds of years. It was very cool to see the sheds where it’s made, where the tweed is made. That was a fun trip and a cool thing that I think some of your listeners might be into. That will be on news stands in two weeks and online around that time, too.

Brett McKay: Cool. David Coggins, thank you so much for your time. It’s been a pleasure.

David Coggins: Thank you. My pleasure.

Brett McKay: My guest today was David Coggins. He’s the author of the book, Men in Style: Essays, Interviews, and Considerations. It’s available on and bookstores everywhere. You can find out more information about his work at Make sure you check out our show notes at, where you can find links to resources, where you can delve deeper into this topic.

That wraps another edition of the Art of Manliness podcast. For more manly tips and advice, make sure you check out the Art of Manliness web site at If you enjoyed this show and have got something out of it, I’d appreciate it if you’d give us a review on iTunes, or Stitcher to help us out a lot. As always, thank you for your continuing support and until next time, this is Brett McKay telling you to stay manly.

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