Why Successful Men Still Dress Badly | Dan Trepanier | EP 15

0:00 And so now when I walk in the room a year later after going through this transformation, it's a totally different reception. It's e- entirely different. Like I could, I could be dressed to the nines and say nothing, and people would assume I'm smart and, and successful, right? You don't have to say anything. Every result has a price. Every goal requires a choice. Comfort keeps you where you are. Discipline takes you where you want to go. Welcome to Discipline Over Comfort with Bob Terrio. Real world conversations on leadership, business, marketing, and execution.

0:32 So today's guest has built his career around something I think a lot of successful people underestimate: how you present yourself. Dan Trepanier. Am I saying that right, Dan? Trepanier. Thank you. Thank you. I knew I was gonna trip that up, but Dan Trepa- Trepanier is the founder and CEO of Articles of Style. He spent more than 20 years studying menswear, style, personal presentation. He studied psychology at Columbia University, at the Fashion Institute of Technology, and was named Esquire's Best Dressed Man in America.

1:07 But what really interests me about Dan isn't just clothing. It's the psychology behind it. Why can someone spend decades building their career, their business, their reputation, and still have absolutely no idea what to wear? Dan has built Articles of Style around solving that problem, helping professionals create wardrobes that fit their body, their lifestyle, and who they actually are. And there's a much bigger conversation here about confidence, execution, presence, personal branding, entrepreneurship, and discipline, and the difference between fashion and actual style.

1:49 So Dan, welcome to the Discipline Over Comfort podcast. I'm super excited to have you on. That was a killer intro, my man. You did your research. Thank you for that. Man, it's my honor. So, Dan- But I'm happy to be here. So yeah, take it away. I'm all yours, man. Thank you. So, you know, people see you today, and they see Articles of Style, the clothing, the photography, and the incredible polished brand, if I do say so myself. Uh- Please... but I wanna go a little deeper before that. You grew up on a farm in Canada.

2:26 So how does that kid eventually become Esquire Magazine's Best Dressed Man? Oh, that's a good one. Good parenting, maybe. You know, I was, I was like the weirdo. Shout out to all the weirdos- Yeah... out there. And I think my, my parents, my mom mainly was, like, allowing me to lean into it, you know? I was obsessive. I was an obsessive kid. You know, at first it was, like, drawing. I was obsessed with drawing. It was video games. Then it became basketball. And, uh, you know, I wanted to be in the gym for eight hours a day.

2:58 You couldn't get me out of the gym. Like, there was, there was people advising my parents they thought I was weird. They thought I was like, you know, "He's missing his childhood. He's, he's working out too much," and stuff like that. My parents just said, "Listen, if that's what you wanna do, do it," you know? So I was... I, I knew I wasn't gonna be a farmer. Like, my oldest brother, he's taken over the farm. He loves farming. He'll talk to you about farming all day long. In his free time, he's thinking about it.

3:24 I just didn't ha- I didn't have that in me. And, uh, I always loved clothes. I wanted to do something different, so I saw basketball as kinda my way to a new life, and I dug all the way in, and my parents were just, supported me, you know? Even though it was, it was, it was very strange for, for where I grew up, you know? Yeah. So was style even a part of your world growing up, or where did that come from? Yeah, I think, you know, I learned early from my mother, who grew up dirt poor, had to make her own clothes.

3:53 She was buying fabric and sewing her own skirts and things like this, and I was watching her do that. Um, so it was always kind of... Like, she was elevating her life. She got a job at the local bank in the small town where we grew up, and that was a big deal, and so she made her own clothes, and people would compliment her, and she, even though she was, you know, from nothing, she looked the part, and she grew. And I kinda watched her just hustle that, you know, hustle through clothes and presentation and, and growing your career.

4:24 So I always knew, like, she's putting in the effort, and she's obviously seeing, seeing benefit from it. And I applied that to basketball. Like, even when I was a, a hooper, it was, like, really important what you wore. Like, it was part of your psychology. It was part of you feeling like the man and people kind of treating you that way. I mean, it was streetwear and triple XL. You know, it was a very different style, but it was very important still even though it, it wasn't about the same clothes, but the mentality was the same.

4:54 So it's, you know, it's the good old, like, primetime Deion Sanders. Like, look good, feel good, play good, get paid good, you know? And that's- Mm-hmm... that is true no matter where you are, you know? Yeah, absolutely. So you ended up at Columbia University playing basketball. What did basketball teach you that you still use today as an entrepreneur? Oh, that's a good question. I mean, any sport at a high level is going to, is going to be a good experience to teach you what it might take to be an entrepreneur.

5:28 You're talking about long hours. You're talking about discipline. You're talking about different parts of your skill set. So you need to be strong. You need to work out. You need to be lean. You need to be athletic. You need to have good ball handling and shooting, and you're spending time on all these parts of your business, right? And then i- also losing, right? Like- Oh, yeah... you lose a lot. You know? [laughs] Like, I've, you know, I've resurrected this business several times over the past 12 years or whatever, you know, through COVID and You lose, you know?

6:01 That life, life goes, you lose a lot, and those who keep playing and keep fighting, um, grow from it and eventually become the winners if you don't give up kind of thing. So it's so applicable in so many ways, right? Like time management- Mm-hmm... working through pain, putting in long hours, dealing with teammates and team. And so, you know, that's why a lot of people like to hire athletes or former athletes, right? 'Cause they've been through the shit. They know they can take a punch. Mm-hmm. Uh, and I don't-- It's not just sports.

6:32 Like I, a lot of times people say, "What's your advice for kids that wanna... What's your advice?" You know? I, I just say, "Just work really hard at something. Be great at something, and put as much time as you can into that one thing you love." Be- And if that doesn't turn out, like it didn't-- I'm not a basketball player. It didn't turn out for me, but I learned so much through that experience that I can now apply it to whatever the next phase is, you know? So whether it's sports or something else, you gotta dive all the way in.

6:58 The, the earlier you do it, the better, and you'll just come out stronger on the other side, you know? Mm-hmm. So you studied psychology at Columbia before eventually studying menswear, menswear design actually. And so when I look at you today, uh, there's two things that actually seem incredibly connected. So how much of personal style is really psychology? Well, psychology in, in some ways is everything, right? Like the way you experience the world and I experience the world is different just based on what we're seeing, our past experiences, how we, you know, how we interpret things.

7:37 So style and psychology are one and, one and the same, you know, i-in some ways. Like people are gonna look you up and down and they're gonna say, okay, they're gonna make a snap judgment about you. And that happens all day long with everyone you meet, whether you like it or not. And- Mm-hmm... you know, if you can, if you can tilt the scales in your favor on that, then it's worth it, right? Like that was my-- So w- you know, going from a farm kid to a basketball kid to an Ivy League in New York City kid, what, that was the big jump.

8:06 And when I showed up on campus, people thought I was like some idiot, and I was. You know, I'm, I'm like the kid from 21 Jump Street. I'm wearing the hat sideways and I'm wearing like the streetwear and I don't really belong there. Mm-hmm. So there's a stigma against the athletes already 'cause we jumped the admissions. Like we didn't have the grades that our other students at the school did. So there's a bit of a stigma and I could tell like, oh, people think I don't belong here, you know? So that was one of the first like, okay, I'm not gonna let that...

8:34 I'm not gonna walk into every room in New York City and be treated like, you know, the white boy gangster kid that's an idiot, you know? So I, I changed my style. Literally, I went from streetwear and learned more about menswear and tailoring and classic stuff and stuff that is associated with intelligence and success and wealth and... So now when I walk in the room a year later after going through this transformation, it's a totally different reception. It's entirely different. Like I could, I could be dressed to the nines and say nothing and people would assume I'm smart and, and successful, right?

9:11 You don't have to say anything. Yeah. As opposed to being the guy who's dressed inappropriately talking too much. It has the opposite effects, right? So I learned that not in the classroom, but in the classroom. You know what I mean? Mm-hmm. Was there like a change that-- Was there an impetus to that? Like, oh, what was that realization that made you go, "I'm gonna start dressing this way now," or was it just a slow progression of your learning? I mean, it was immediate. It was immediate, right?

9:44 Like I could tell right away. Right. Like I walk into a room and the way I'm getting looked at is like they think I'm a fool, you know? So I knew right away that I- Hmm... I was out of place. Like I really was fish out of water. So that was, that was the reality of the situation. So I knew as soon as I got on campus, I was like, "Okay, this is-- I need to make some changes." Now it took me a while to figure out what those changes were, and I put in a lot of effort there, mainly buying clothes secondhand, sample sales, eBay.

10:16 I had no money, but I was really trying to change my style. Learned about tailoring, local alterations. Test, test, test, test, test, you know? And uh, so the s- the, the, the, the, the experience of knowing I needed a change happened right away, but it probably took me a year or two to really... It was, it's goofy at first, right? Like every guy who's tried to update their style, the first phase post wanting to upgrade is pretty goofy. Like you're doing too much. Mm-hmm. You're doing way too much.

10:48 You don't understand the subtlety. So you're doing the loud colors, you're doing the bold patterns, you're doing the f- you know, just out of place a little bit. So you go, kinda go through that. Peop- You know, you get the feedback, you get compliments, you feel it out, and then you, you sort of refine it over time. Still refining it today, right? But- Yeah... um, it's a, it's a work in progress if you... And you change too. Like I'm not dressed in the same way I was when I was 30 or when I was 20.

11:16 It's kind of an evolution, you know? Mm-hmm. Yeah. So I wanna settle something right away. So what's- [laughs]... the difference between, between being fashionable and actually having some style? Well, like fashion and style are very different words, right? Like fashion is an industry, right? The fashion industry. Fashion is a cycle of design and fashion shows and collections. You know, Gucci fall winter '25 is a certain color palette, a certain fit, a certain look. This is a, a whole machine. I personally don't like the fashion machine.

11:52 I think it's detrimental to the consumer and beneficial to the brands because what they're doing is basically trying to change the formula every season to get you to buy new things. That's why one season it's about the skinny pant, the next season it's about the wide pant. We're in the wide pant trend right now. Things just- Mm-hmm... change very quickly, right? So my thing is, like, style as opposed to fashion is, is much different word in my opinion, 'cause style is more about how you do things.

12:22 Like, you can walk with style, you can talk with style, y- you know, you can, you can move with style, you can play basketball with style, you know? Like, look up- Mm-hmm... Jason Williams. Like, that guy styles through the roof on the court, you know? Mm-hmm. So it's... They're, they're very different things. You can... The most stylish people, in my opinion, don't follow much of the fashion scene. Like, they don't worry so much about what's in trend or what's this season or... They're thinking a lot more about themselves, like their body, their coloring, their career, how they move around the world, how much they travel, and those clothes are appropriate for them regardless of what's going on, you know, on the runway.

13:02 Yeah. And it's how they carry themselves, right? Yeah, and you can feel it. Like, if you feel someone that's really into fashion, it's almost off-putting to me. It's like, oh, he's like a fashion victim. He's so up to speed. Mm. Like, you know this guy's- Mm-hmm... shopping all the time. Like, he, he doesn't even have his own identity. He's just kind of wearing costumes from the designers. And when you feel someone- Yeah... with style, it's like a whole different experience. It's like, whoa, that guy is fucking smooth, you know?

13:29 Like, he's just- Mm-hmm... he's not even doing anything. He's not even really talking much. The way he moves, the way he sits, the way he dresses, the colors he picks, it's all just very... It just makes it look easy. It's like watching a guy just move through the world in a way that's like easy 'cause it's just like it's him and he understands how he should be put together, you know? Yeah. And in my opinion, Dan, I don't see that too much, do you? I mean, out in the wild. No. No, I think we're probably in the worst style era ever.

14:01 Like, I think we've... And I've done a, I've done videos about this. I think we're kind of, we've peaked bottom, you know? I, I did a video called Peak Shit. We're in the peak shittiest moment, you know? Peak shit meaning it's the peak of the, of the amount of shit that we have and the lowest quality. So, you know, we, we've really dug deep in the fast fashion. A lot of people,

14:26 you know, are starting to care again, I think. You know? We kinda came outta COVID. It was comfort clothes, it was gym clothes, it was golf attire every day. It was kinda what's easy. And now I think we're- Yeah... we're coming out of that a little bit with people saying, "Man, I'm kinda tired of wearing this stuff. I don't feel good wearing this stuff. I look like everyone else. I'm not getting d- I'm getting disrespected. I don't..." You know what I mean? So I think we're- Yeah... rediscovering...

14:53 We're, I think we're rediscovering clothing in a way as we just hit such a casual environment in, in everyday life. Yeah. But to answer your question, no, it's very rare. It's very rare to see a person, especially a man, and be like, "Damn, that guy is really well put together." And because it's so rare, it's like an amazing feeling. Like, you c- it's like being a superhero, you know? Like, you can be out there, and if you got it together, it's like people are, like, complimenting you everywhere you go.

15:22 It's like, it's like you stand out so much just by having a fucking tailored jacket on, you know? Yeah. Not only that, but you can also make 'em feel very uncomfortable. Well- I've noticed that. [laughs] Yeah, I think people, you know... The discomfort that people feel is them actually wanting to be like you, right? It's like you're making them like, "Man, I wish I had the balls to, like, try that," you know? It's not like they dislike you. Yeah. I- i- it's like, it's, it's this feeling of I'm lesser for some reason and I wish I was better, you know?

15:54 So I- Mm-hmm... I always just encourage people, "Hey, man, there's no need to be mad at me for being put together. Like, I... You know, we can all do this," [laughs] you know? I don't know. It, it's like- Absolutely... that's another, that's an example of things from sports. That, that's another good example, right? Like- Mm-hmm... I deal with this everywhere I go, right? But, like, when I was a basketball player, it was like, "You're never gonna be good enough." Like, well, it, it's the same. There's haters no matter where you go, you know?

16:17 And, and a lot of people with fashion, they, they don't wanna deal with that. Like, there, there's... Y- you really just like, uh, it's group, it's groupthink. Like, you wanna fit in and not deal with that. Mm-hmm. And I think a lot of guys are just getting kind of sick of where it's at, you know? Mm-hmm. So your website identifies this interesting... I, I guess it's a contradiction. A guy can be extremely successful, he can run a company, he could build wealth, manage hundreds of employees, make, make incredible decisions, and yet his closet can be complete chaos.

16:52 Why does this happen? [laughs] That's a good question. It's truly unbelievable how many guys are out there that are, like, well put together, intelligent, got their shit together, white picket fence, beautiful family, brand-new car, and the guy steps out of the car, is wearing, like, you know, flip-flops and, like, you know, the, the Lululemon ABC pants that everyone else is wearing or whatever, right? Yeah. Um, I think the answer is it, it's, it's hard, right? It's hard to, it's hard to build a good wardrobe.

17:30 It takes a lot of effort, a lot of time, and it's harder than ever. Like, stores now are terrible. Like, you walk into your local store, no matter what it is, Nordstrom, Saks, whatever, the buy, meaning the selection that the store carries, is, is very minimal. 'Cause people aren't going in the same way, they're not shopping at the same rate, so they're not taking as much risk on cool products, so they're only gonna have the very basic. They're gonna have the blue and the gray, and then by the time you find your size, there's only a couple options.

17:58 And then the people in the store that's supposed to help you, they don't know anything. So- Yeah... and now, now you're trying to build a w- cohesive wardrobe with different brands, different fits, different color palettes. It's all mish-moshed- And then the rules have changed. Like, what does business casual even mean? Like, so many guys wish it was just suits and ties like it used to be 'cause it was so much easier. Now th-th... You don't know what to do. And, and then guys shop in, you know, impulsively.

18:23 They buy one item at a time. They buy the shiny object. They collect a bunch of weird things in their closet that don't work together, so they don't wear it. They default to the lowest common denominator, the same old thing. They wear the same 10% of their wardrobe over and over again, and they just don't know, they don't know how to, how to get out of that cycle. Like, where do you go to get a good wardrobe if, if you haven't studied this stuff, you know? Yeah, you do. But I think this is, like, the perfect segue for you to talk a little bit about, say, articles of style.

18:54 You know, somebody's just jumping on here, you know. This is on a bunch of platforms, on YouTube, it's on Spotify, Apple, it's everywhere. But if somebody's hearing this part, I think this dovetails into your business, your company. Can you explain exactly what it is you do? Yeah. We're, you know, we're the guys that take care of your wardrobe from soup to nuts, right? So what I do is I'm a trained tailor. I'm a custom clothier. I'm not... I shouldn't say I'm a tailor. I don't like to say I'm a tailor 'cause I don't actually make the clothes.

19:25 I don't even like to call myself a designer 'cause I don't make the patterns. That's not here nor there. But I meet with people on Zoom- Mm-hmm... to start, I have people all over the world. I get to know people. That's the main thing is we actually care about our clients. We get to know them, and then we design wardrobe packages that are ideal for their life. So we're like a custom clothing shop meets a personal stylist, but we do the full wardrobe. You know what I mean? So we do shirts and sweaters and polos and all of it.

19:54 And then we have an online fitting process that w- that we do that is very unique. So it's custom clothing kind of for your whole wardrobe, if that makes sense.

20:05 Yeah, absolutely. I mean, I f- I found it interesting. You know, when I was on the website, I was like, "Hmm, they've... It seems like they have this system down pretty pat." Well, you know, the, the idea of the capsule wardrobe is all the items work together. That's the main thing guys struggle with is they don't know what goes together. I mean, we're, we're kind of solving all the problems, right? Fit is a huge problem for guys. They can't find stuff that fits, so they don't know how it should fit on their body.

20:30 So we do custom fittings from home. That's first and foremost. And then two is the personal styling element, so the coloring, the fabric. Like, if you live in Florida, you're wearing very different fabrics than if you live on the East Coast or something, you know? So the weight of the fabric, the colors of the fabrics, the style of the garments. Are you a suit-and-tie guy? Are you a casual guy? Like, we have guys that don't wear suits at all. Like, they're, they're in the tech industry, but they still wanna wear nice clothes.

20:55 And it's not- Mm-hmm... formal attire necessarily, but they just don't... Like, they're wearing, they're wearing very cheap stuff they don't like, and they can't find good clothes. So we come in and say, "Hey, here's, here's what you need." You know? "Here's the right fabrics for your climate, the right colors for you, the right designs, the right fit for your body." And we just solve this problem. Ideally, our clients, they don't need to do anything. Like, they can get dressed in the dark. They wake up, all their stuff fits, all their pants works with all their shirts, works with all the sweaters, and the coat goes over top.

21:28 And, you know, they have 20 items, but they got 100 different outfits, and they live in this stuff. And they're the best-dressed person wherever they go because the clothes are very intentional. Um, so it's, it's kind of a one-stop shop to solve all these annoying menswear problems, you know? Mm-hmm. What does an average client of yours look like? Is this an executive? Is this just a busy professional? And I, and I was also surprised because I saw that you, you guys have bespoke clothing for women as well, correct?

22:01 Yeah, we do women as well. Yeah. Predominantly men. Well, I mean, we make menswear for women. So all of the garments on our website can be made for any body, including a woman's body. But we're not making, like, sundresses and stuff like that. It's tailoring. Yeah. Average client... I mean, the client base is all over the place. That, that's kind of the best... That's the most fun part about it is, like, I, you know, I'll meet with a guy at 10:00 a.m. He'll be, like, a US senator, and then I'll meet with a guy at 11:00 and he'll be, like, a UFC fighter.

22:34 You know? Yeah. Like, you, you just never know who the guys are. A lot of hard-to-fit guys, obviously, and frankly, a lot of guys that are in small markets. Like, some of our, our most common customers are, like, professionals, doctors, lawyers, wealth managers, finance guys that live in, like, Ohio or Wyoming or just, like, the middle... You know. People have moved out a lot, and the shopping just sucks. So what, what are their options, right? Like, they make good money, but the store locally is terrible.

23:07 Mm-hmm. And they shop online. The stuff doesn't fit. They don't know what to pick. They're constantly buying online and shipping and returning and dealing with that. So they see me and us as this is, like, the experience of walking into a personal stylist or a custom tailor, but I can do it from home. So, like, when you do the math and figure out what we're offering, like, it does- it really is a no-brainer for that guy because he's not gonna be able to do it on his own, and he doesn't have the time.

23:36 He doesn't have the time to do it. And he's, he's been trying to dress better, but he's really struggling, you know? And he, he never feels good about it. So yeah, I- I think it's a really smart concept. I mean, I, I, I love the concept. Yeah. It's, you know, we got there over time, right? You iterate. Like, we, when we came first... When we started the business, it was all about just doing fittings. So we were trying to do the best fitting suit online, period. Highest quality suit, best fit. We do a fitting process where we make a, we actually make a custom-made test garment.

24:08 We send that to you. We review that. We look at it on you. We ask you how it feels. We make all the adjustments. That was our initial, like, come to market. Like, we're gonna be bespoke online from home. And- Mm... you know, we ironed out the fitting process. We were doing really well with that, but our customers just needed, they needed more help. Like, "Okay, when I'm not wearing a suit, what do I wear? Like, what about casual wear? What about polo shirts? What about sweaters? How do I... You know, I don't want just to look good when I'm going to a special occasion.

24:40 I want my whole wardrobe to be dialed in." So over time we added the more casual items. We added the knitwear. We added, you know, a lot of things now. Uh, and then we kind of came to the realization that what the guy actually needs is like a package, like a, a cohesive wardrobe that works together and is designed for him. So the capsule wardrobe thing is a, is a relatively new concept for us that we came to from customer experiences. Yeah. I, I think it's a great concept. I love it. I think it's very cool.

25:13 Nice. Where, where are you based out of? I'm in Toronto, or I'm in the suburbs of Toronto. But we're a- Okay... purely digital business, and our team is kind of all over the place. So we are- Yeah... very much a true digital nomad type of operation. Yep. A lot of businesses are like that. Well, we weren't... You know what? We started that way, 'cause I was, I was an early blogger. Like, my background was when I was playing basketball in college, I started a blog that blew up because I won the Esquire Best Dressed in America contest.

25:50 And then I had readers from all over the world that were flying to New York for me to style them. So that was the initial, like, this is... There's an opportunity here, right? And it was always online. Like it was a, it was, it was an internet thing. And there's a whole another story about how we did open a store in New York. We had a store in Soho for three years that I didn't enjoy. I didn't think it was a good move for us. COVID happened. We closed it and went back to online. But we-- I always knew that the, the, the opportunity was personal service online.

26:25 Like, if you can help someone one-to-one and share your actual skills, your fitting service, your styling service, get to know them, provide a human connection through, like, this way, then- Mm-hmm... there's an opportunity there because almost every internet business or e-commerce business is, like, all about automation, right? Yeah. Like, no one cares. No one looks at anything. You measure yourself. You plug it in. You pick your fabrics yourself, and it's very low quality. It's very quick. So it was obvious there was an opportunity for higher service, higher quality, but take advantage of, you know, the convenience and reach of e-commerce.

27:05 Mm. Yeah. I saw a, uh, Business Insider story published last week, and I thought I'd ask you about it. The story was about professional men and how they've been obsessed lately with the quarter zip. So search interest for men's quarter zips has increased more than 300% in the last five years. [laughs] And the article describes it as this middle ground between formal and casual. What one person said in the interview was that it's comfortable sophistication. And- [laughs]... that, that, that one line really caught my attention.

27:41 [laughs] So a blazer says-- It says, "A blazer says I tried, a hoodie says I didn't, and the quarter zip somehow says I didn't try and I still look good." So we've gone from suits and ties to quarter zips and, uh, and sneakers in a lot of the workplace, right? So would you say that's progress since COVID? Man. [laughs] I mean, the quarter zip...

28:15 I was in New York not that long ago and I was at the, a steakhouse, and Alex was there, Alex Kroff, who has with Guy from Gladsen, and Alex was there. Our, our... It was, it was our fabric vendors were taking us out to dinner, and it was my team. And you know, we're the Articles of Style team. We wear, we wear cool stuff. We wear unique pieces or whatnot. And we looked around the steakhouse, and it is Midtown Manhattan. This is 53rd and Park or whatever, you know? Okay. Put that just as a caveat.

28:44 Every table had a guy in a quarter zip. Like, like literally every... We said, "Is there a table in here where there's not a quarter zip present?" And there wasn't. You know, it's the, it's the finance uniform. It's, it's the smart guy. Yeah. It's, you know, it's, it, uh, it feels safe. Like, there's a whole other story about the quarter zip where the young Black kids were, like, getting out of the streetwear and wearing the quarter zips and they were, you know- Mm... talking about how it's life-changing and people are, you know- Mm-hmm...

29:09 trusting them more and thinking they're smarter. And it, it happens for, you know... That's true for anyone I guess. Like, it's just one of those items that is like... It's just like a symbol. Uh, to me it's very basic and I, you know, I don't like it because it's so... It's just like a uniform for a certain type of career- Mm-hmm... you know, in the business casual and, and, and finance world. It's kind of like the Patagonia vest. Just similar, right? It's like- Yeah. All the finance guys- So no, I think to me it's, it's, it's way closer to the hoodie than the, than the blazer in my opinion, you know?

29:48 Like, knitwear in general is always going to read very casual and very laid back. So I don't, I don't see it as something very professional. Mm-hmm. Is it progress? I mean, progress... Is it progress from COVID? Sure. I mean, what's not progress from COVID? I, I wasn't even wearing pants. I mean, like anything is progress from COVID. Yeah. I was disinfecting my groceries wearing boxers with holes in them for weeks at a time. What do you mean? Of course. [laughs] It's- People were on Zoom in underwear.

30:19 Yeah. Like we, you know... Sure. Sure. Progress. Yeah. [laughs] You know, we got out of our underpants, so we're- We're progressing, I guess, but, you know, I think that- So do you, do you think that the quarter zip is actually like you're gonna look back at pictures to 2026 eventually and say, "What the hell was everyone doing?" No. No. I mean, quarter- 'Cause it's not going away this season... quarter... It's not going away. It's also been around a very long time. Like, the quarter zip is not a new thing.

30:50 Yeah. You can look back to vintage pictures of menswear and there's some version of a quarter zip. My thing is just so, it's so ubiquitous now. It's just like it's a bland, like it's a, it's a personality-less or character-less item, right? So I don't, I don't like that version of fashion where you're trying to fit into the group. A, a lot of people, that's what they want from clothes, and that's fine, you know. But I like to dress the guy that has a little bit more unique identity, wants to portray a unique identity, uh, and wants to kinda stand out from that sea of Patagucci vest, quarter zips, you know, just what everyone else is kinda doing.

31:31 So how do you, how do you advise those incredibly successful people who wear basically the same T-shirt, hoodie, and jeans every day? So somebody watching this might say, "I'm good at what I do. Why should I care about what I'm even wearing?" What, what do you tell that person? That's not even my guy, you know? Yeah. Like, the... Yeah.

31:59 I think you gotta, like, you're not, you're not gonna... As a clothier, you're not gonna convince a guy who gives zero shits to, like, start caring, you know? Like, they have to come to that on their own, you know? Like, you can tell a guy, "Hey. You're gonna feel better about yourself. People are gonna respect you more. It's just, you know, whatever." But, like, if he really doesn't care... U- usually, usually it happens, like, like I'll catch guys wanting to upgrade after certain key things happen, you know?

32:31 Like, like if that guy goes to Europe, then that's gonna be a moment for him, you know? Hmm. Like, that happens all the time. Got a lot of guys newly retired, went to Europe for a few weeks for, like, my first trip, and I felt like such a fish out of water. I looked like- Mm-hmm... the American tourist. I'm getting disrespected, and I just, I just, I don't want... And they're like, "Wow, these guys in, in, in England and Italy, they, they look amazing." You know, so they're, they're, they're both feeling like shit about themselves, and they're seeing other guys doing it well, and they're like, "Okay.

33:05 Well, maybe it's my time to step up." So that's, that's a very common one. Obviously, career change is a common one. Weight loss is a common one. Divorce is a common one, where they're kinda like reassessing, you know, their, their whole image. Yeah. So if the guy's, you know, dressing like shit, doesn't care, doesn't wanna upgrade, I'm not even trying to convince that guy that he needs to change anything. Yeah. You know? If for some reason he's not feeling his best, he thinks he can do better, he's had some of these experiences, and he has the inclination to want to improve, now I can help you.

33:41 But I'm not here to tell you you're not living the right way. So let's, let me make this a little personal. I've, I've got, I've got you here on the show. So I'm 57. I'm a marketing executive. I host a podcast. I'm on camera. I work with business owners and executives all day. If I hired you tomorrow, what would you wanna know about me before you recommended any single piece of clothing? That's an excellent question. My first sort of initial questionnaire is how you look. So skin color, hair color, eye color.

34:18 That's huge 'cause that's gonna... That's the first, kinda the first thing 'cause that's gonna inform the color palette, if you will. And then the next thing is where you live and where you travel to and, and mainly what the climate is there. 'Cause like I said, a guy in, in the South and, you know, super humid Tennessee is, it's gonna be very different than a guy in Northwest or whatever. And the clo- I'm in far West Texas. Yeah, exactly. Exactly, right? You're out there by fucking Marfa, Texas, or wherever you are.

34:49 Yeah, El Paso, Texas. So, yeah, so immediately it's like, okay, all your fabrics need to be very lightweight and very breathable off the jump, right? And then it's your career. Like, what do you do for a living? How, how do we need to look? How professional do you need to look? Like, what, what's the vibe you wanna give when you meet a client? Do you wanna look like you're extremely sharp and put together? Like, it's very important for certain types of careers to look like your details are, are, are on point, you know?

35:17 So those are sort of some of the first questions. Then I ask you what's in your wardrobe now. Like, what are you doing now? What do, what do you wear Monday to Friday? What do you wear Saturday, Sunday? That informs me what kind of brands you're buying, what's your kind of vibe. And then I ask you, "Okay, what's your ideal?" Like, who is the guy you look at like, "Damn, that guy, if I could be like him, I would, I would feel amazing"? And it doesn't have to be a real person. This could be James Bond, you know?

35:41 This could be, could be anyone. 'Cause that gives me a sense of where you're at, where you wanna go, the colors and the fabrics and the weights that you need, the professionalism, whether it's suits, sport coats, bomber jackets, shackets, polos, whatever. So that's the framework, right? And then I design... Then your budget, of course, right? Like, how many, how many... We have different sizes of packages, and I, you know, walk you through that. And then I, you know, then I put together kind of a first version and say, "Hey, if I was you, this is the perfect wardrobe.

36:15 Here's the five shirts. Here's the three jackets. Here's the 10 pants, the two coats. You don't need any coats. It's all gonna be lightweight for you." But you get what I'm saying. And the idea is- Mm-hmm... all these pieces work together. Literally. Like, you can't make a mistake. You can get dressed in the dark, takes you two seconds, boom. It all goes through the fitting process. Obviously, there's a whole section of fit that I didn't talk about. Your height, your weight, measurements, how things fit you.

36:40 What some of the common issues you have are... Like, you look like you're pretty muscular, so you probably have lapels lifting very often, right? Tightness in the armhole, right? You know. Yeah, exactly. Collar rolls. So a lot of guys have the same frustrations because they're wearing ready-to-wear that's not cut for them. So if they're a little bit different than the average, it's the same problem over and over again. "Every time I put a jacket on- Yeah... there's a huge roll in the back," you know, or whatever.

37:04 Um, so that's what I mean, that's what I mean by getting to know you. And then I kind of make a, a suggested capsule, and then we edit that together. It's, it's very much a collaborative effort. Like, I'm not telling you what to wear, I'm suggesting things based on what I know about you and what you already have, and then we go back and forth. You might be like, "Hey, I don't... I would never wear this color. I don't like this jacket. I already have a pant like this." So I'm trying to, like, make the perfect wardrobe for you based on who you are and what you have and where you wanna go, you know?

37:37 Yeah. Yeah, it sounds like a seamless process to me. It's... We, we, I mean, we've done it many, many times now, so we're pretty- Yeah... honed in on it. But it is a puzzle. It is a puzzle. Like, every w- every guy is very different, you know? Obviously body types, how much they travel. Th- there's a, there's a lot to it. And then some guys just have weird preferences. I shouldn't say weird, but unique, you know? Like- Yeah... and lifestyles. Some guys are vegan, they don't wear wools or... Whatever it is, like, there's, there's often some uniqueness to the situation.

38:11 That is kind of the fun part of the puzzle. And then when you nail it for the guy, now you got a customer for life, right? Like, like, "We're delivering clothes out here that are the best clothes this guy's ever had. I've never gotten so many compliments. I've got promotions. I've met a new girl." Like, there's, there's so much of that, and that's like the f- makes it kind of rewarding, you know? And then obviously you save- Yeah, those are cool stories. That's what you do it for, you know? Yeah.

38:37 And then, uh, and then you have a customer for life. Like I said, like, w- w- we got your wardrobe tracked, we got your fit tracked. I'll hit you up in six months, "Hey, how's the stuff working out? You got anything coming up this season? You need a coat for winter?" And we just become the sort of like, the guy, the solution to, to, to help you with your wardrobe, you know? Very cool. I, I followed you. I found you on TikTok, and you made a... So the next question I'm gonna ask you is, it, your TikTok inspired the question.

39:08 So- [laughs] Okay... if you could fin- if you could finish this sentence for me. Most men should stop buying blank, and why?

39:19 Synthetic fabrics, I would say. I would say synthetic fabrics. Okay. They're just- Why is that? Well, a number of re- they, they don't perform well, they don't breathe well, they don't drape well, they look like shit, they, they don't wash well, they fade a lot. They're not good for the environment, they're not good for your health. You know, every, every sense... It hits every sense, you know? It doesn't look the same, it doesn't smell the same, doesn't feel the same, doesn't sound the same. You know, your pants are swishing around when you walk, you know?

39:49 [laughs] And I think, and I think a lot of fashion brands have taken advantage of people that aren't super educated on clothing and have dropped the quality or replaced natural fibers with synthetic ones because the, the, the, the cost difference is insane. Like, like, to get a really nice wool fabric, right, it's gonna be probably 80 bucks, 100 bucks. It goes up tremendously more per... And when you're doing these lab-created, it's essentially an oil product, it's like a couple cents, you know?

40:20 So even it's, it's purely for the bottom line. And yeah, I think it's, I think it's probably the easiest way to find clothes that you really love if you go back to just high-quality natural fabrics, you know? The other easy answer to that question would be stuff that doesn't fit. Things that aren't your size. Yeah. Like, so many guys are wearing the wrong size. Mm-hmm. And again, it's because it's very hard. Like, if you have... A lot of guys have, like, strong legs, they have big thighs, big glutes or whatever.

40:51 You're buying-- You're probably wearing pants that are too tight because they're- Mm... they're not made for you. And you're, what you should do is be sizing up probably two sizes to fit the seat and thighs and having the waist taken in by a tailor. But, like, most guys aren't gonna go through that trouble, so they're squeezing into some super tight pants that just, again, they're not comfortable, they don't look good, they're not gonna last well. Uh, and it just doesn't give you the feeling of wearing something that's, like, meant for you and draping around you.

41:18 It's really just kind of, like- Mm-hmm... glued to your legs, you know? So I have, like, a two-part question. So does expensive actually mean better? Like, how can I tell the difference between something that's genuinely well-made and something that's simply expensive because of the name on the label? That's a good question. It does... It probably takes some experience. I mean, I c- I can tell right away, right? Like, I can look at it- Yeah... across the room and tell. And a lot of people can. People that are educated about this stuff, they can tell.

41:58 If you can feel it, if you've felt a lot of garments, you can start to tell, right? But looking at the fabric composition is huge. And again, there's levels to everything, so just because it says 100% cotton or 100% wool doesn't necessarily mean it's a high-quality one, but that's better than synthetic, again.

42:18 And, you know, without visuals it's hard to show you, but there's certain things you can look for in the way, like, zippers are set or inlays are done or fabric allowance is treated. Like, if you, you can start to see things like- You can see the edge of the seam allowance that's pressed against the side of the jacket. Things like plastic buttons, that's, that's a dead giveaway. Plastic zippers. Like, if they're using plastic buttons and plastic zippers, they, they don't care enough to give you, you know, horn and metal.

42:47 So they're cutting, they're cutting costs heavy on the production, right? There's certain details that are very simplified in garments, like a jacket that doesn't have a proper vent in the back or working button. Well, there's a lot of, like, small details like that. But for a novice person to tell, I would look at fabric composition for sure. And frankly, like sometimes you just have to look at the garment, you know? Like I, I... Like, if you hold up a really cheap garment versus a well-made garment, it, it looks very different.

43:20 Mm-hmm. Mm-hmm. Like, a cheap garment is going to be very flat looking. Like, it doesn't have any dimension. Lapels don't roll. They're pressed flat, you know? The sleeve falls, like, very straight down. It doesn't curve out. You know? Like- Mm-hmm... a beautiful garment on a hanger is gonna look beautiful. It's gonna, it's gonna s- fall nicely. It's not gonna have wrinkles. It's gonna have a nice shape to it. It's gonna have dimension to it. But again, like I said, like, if you don't know anything, y- you have to do your research and study this stuff a little bit to, to be able to tell the difference.

43:53 It's like anything. It's like, okay, look at two motors and tell me which one's better. If you know nothing about motors, it's like, okay, that's- Yeah... gonna be tough, you know? And, you know, most guys aren't gonna do what you just talked about. Like, that's why I think the, the content ag- that you give on TikTok or I- um, Instagram, I'm sure you're everywhere, but the stuff that I've seen is... I saw you on Instagram a- also, but it's very informational. So, like something like that, I think it's great content.

44:18 Has social media made it easier for you to teach men about style? I mean, I'm sure you get a lot of feedback, right? Yeah. I mean, my thing is teach it first, you know? Like, if we can... That's how you get a customer. You become the expert by teaching them, right? So you don't hold back information. You try to give it all away. Mm-hmm. Like I, you know, like I, I have all... Here's a shameless plug. I have an e-book that is, like, my top lessons or my top blog posts that I've re- kind of updated as, like, here's everything you need to know about menswear.

44:49 And it's a guide. It's a guide that allows you to learn this stuff. And I, you know, I sell it for, like, $7. I, I'm gonna make sure to put that link in the show notes. Dan, I'm gonna put the link to that book- Yeah, yeah... in the show notes, okay? That's a great place. That- Yeah... that's a great place to start, right? It does answer some of those questions about determining quality, how things should fit different body types. It, it's pretty in-depth. It's like a 200-page e-book or whatever, you know?

45:09 And I sell it for, like, seven bucks. And what happens is, like, guys will buy that, and they'll try to go shop themselves, and they'll do better than they were before. But then, you know, they hit roadblocks where it becomes hard to build a great wardrobe. And eventually, some of the guys will reach out and say, "You know what? Why don't you just do this for me because I know you're gonna do it better than I'm gonna do it on my own." So and I talk about this with content. You really should be educating people.

45:35 You should be providing value- Mm... with your content. Mm-hmm. And the guys that eat it up and love it will ev- some of them will eventually become your customers. So that's the best form of marketing, in my opinion, is if you can both educate and entertain, uh, ideally, and show that you're a personality that is easy to communicate with. That's how you become known as the expert, right? And your book is How To, How To Buy Menswear: A Guide to Escaping the Fashion Trap and Building a Timeless Wardrobe.

46:07 So what exactly is the fashion trap? The fashion trap, like when you, when someone says you're a fashion victim, like that's a common term. It means you're in the cycle, like you're on the hamster wheel. Like we talked about earlier, like you are buying things because fashion brands are telling you they're cool. So you're wearing a lot of logos. You're wearing a lot of this season's colors. You're wearing a lot of this season's fits. And then next season you're gonna throw out some of that stuff and then buy it again.

46:36 So it's a trap because you're not really ever recouping your investment. You're just constantly buying new things. It's very wasteful. It's very time-consuming. It's very expensive. Um, so my thing is, like, buy it once and wear it for 10 years and, and build a wardrobe of pieces like that. Mm-hmm. Has very little to do with the fashion cycle and more to do with you, your body, your, your lifestyle. And then you could actually achieve a great wardrobe where you feel confident every time you pull something out, like, boom, this is, this is me.

47:07 You know? Y- you're not even thinking about what's happening in fashion.

47:14 Yeah. Coming from a marketing guy, you know, I, I see the word timeless used a lot in advertising and marketing, and so they throw that, that term around a lot. What actually makes something timeless in men's wardrobe?

47:31 Uh, I mean ti- you know, nothing is truly timeless, but things are, can be a lot, can last a lot longer than others. You know, Cary Grant said it really well. Like, he was a big... Obviously, he's known as a style legend, but he was actually really into clothes. And his thing was like, "Don't go too far in any direction." Like with lapel width, don't go too wide, don't go, don't go too skinny. With jacket length, don't go too long, don't go too short, right? So there's a middle ground in menswear that's all about subtlety, where it's not, it's not too far in one direction or the other.

48:09 And because of that, it can la- I mean, menswear is pretty simple. You know? Like, there's only so many garments that a man's gonna wear. You know? Like- Yeah... it's not that many. You know? You got your suit, your sport coat. You got your short jacket. That could be a tour jacket, a bomber jacket. You got your long coat, top coat, overcoat. You know, you got button-down shirt, polo shirt, crew neck, V-neck, cardigan, trouser, five pocket pant, jean There's not that much. Like, all these designers are doing spins of those garments, and a lot of the fashion variations are very unique by design.

48:51 Certain logos, certain colors, certain croppings, certain oversize, whatever, to make it very current, and that is the opposite of timeless. So if you boil down those styles and remove some of the things that make 'em overly current, you can get a piece that will look as good today as it will 10 years from now. I mean, I, I wear clothes that's, that's 15 years old all the time. Mm-hmm. And there's a certain joy to that, right? Like, I, I've been wearing this thing. I know this thing. This thing smells like me.

49:20 I remember where I was when I was wearing this. And that's a nice relationship to have with any kind of material good. And it's the type of relationship that is being robbed from us from the fashion industry. And the thing that I love to l- like, the best news I can get from a client is like, "Man, I'm still wearing this thing from 10 years ago." I'm like, "Dude, that, that is a huge win." Yeah. You probably got so much use out of that and so many compliments on that. Mm-hmm. And it probably molded to your body by now.

49:49 Like, that's probably a friend of yours at this point. That, like, as far as r- regardless of timelessness, that's the win, a long-term relationship, you know? Mm-hmm. The name of the show is Discipline Over Comfort, so I wanna bring everything we've talked about back to that. Where in your life today are you choosing discipline over comfort? Oof.

50:20 I mean, entrepreneurship is, is discipline over comfort, whether, whether you like it or not. I mean, there's not a lot of, there's not a lotta comfort. It's a balance, you know? It's a balance. Yeah. Like, anyone who's an entrepreneur knows that there's a million things that come up. You're putting out fires all the time. You have to be very disciplined. Mm-hmm. But y- you have to try to develop your own balance as well. Mm-hmm. You know? Like, you have to enjoy the fruits. You have to carve out some comfort for yourself, but it's hard.

50:52 It's hard because- Yeah... the business is always top of mind. Like, e- e- every entrepreneur says the same thing, right? The guy, the CEO of Anthropic, one of the biggest companies in the world, he did Joe Rogan and he was saying how he wakes up in the morning and he, the first thought he has is, "Oh, we're gonna go out of business in f- like, a- any moment," you know? And, and Joe Rogan's like, "Dude, w- what? You have the biggest company in the world." He's like, "Yeah, but this is a feeling that never goes away."

51:16 Yeah. You know? And that resonated with me, you know? Like, there's a paranoia that is necessary for entrepreneurs to continue doing what they do. That's right. And it's very, it's very uncomfortable. And just dealing with that takes discipline, you know? Yeah. So- Well, I know you have short on time, so I'm gonna do a real quick rapid fire and then I'll let you go. So I'm gonna say something. All right. I don't want you to overthink it, and then you just answer. I know you can go deep on all this stuff, but- [laughs] Okay?

51:48 So- All right. All right... suit or sports coat? Suit. Black or navy? Black. Sneakers or loafers? Loafers. Tie or open collar? Tie. Pleats or flat front? Ooh. [laughs] Flat front. I think flat front. I think flat. Depends on the fabric. Belt or side adjusters? Side adjusters. Wool- Unless you have a great belt... okay. Wool or cashmere? Cashmere. Come on. Watch or no watch? Watch. Trends or timeless? Timeless. You already know. Most overrated menswear trend? Uh, overrated meaning people think it's good?

52:51 Yeah. AB- the ABC pant, Lululemon ABC pant. Most overrated, over-purchased garment of all time. One thing no man over 40 should be wearing. Skinny jeans. One item every man should own.

53:11 Uh, tweed blazer. What's the f- first thing you notice about a guy, what he's wearing when he walks into a room? Uh, the fit of his clothes. Awesome. How'd I do? So Dan- [laughs] Dan, this has been fantastic. I think one of the things that people will take away from this conversation is that really it's, it's not about the clothes, it's about intentionality. It's understanding who you are and how you wanna show up and how you're presenting yourself. So I appreciate it. Again, Dan is the founder, CEO of Articles of Style and the author of How to Buy Menswear.

53:53 Dan, thank you for spending time with us. I'm gonna put the link and your social media. If you could send me that email, but I'll put it in, uh, into the notes. And to everybody watching, if y- if you enjoyed the conversation, subscribe to the Discipline Over Comfort podcast here on YouTube. Uh, we've got more conversations like this coming. And remember, discipline over comfort every time. Thanks, Dan. Thanks, Bob. Great job. It was awesome