Derek 'The Menswear Guy' Guy

Men's fashion might seem like a niche topic. But people of all genders and sartorial sensibilities follow Derek Guy on X for his clothing takes... even if they're not quite sure how they found his page. Endless Thread talks to Derek about how he weaves together humor, history, cultural criticism, and political commentary to make fashion feel relevant to people who have never seriously considered it before. Show notes @dieworkwear (X https://x.com/dieworkwear?lang=en) Die, Workwear! https://dieworkwear.com/ The Post Trend Universe https://www.nytimes.com/2015/02/15/t-magazine/post-trend-universe-cathy-horyn.html (The New York Times Style Magazine) Status and Culture, by W. David Marx https://www.penguinrandomhouse.com/books/659558/status-and-culture-by-w-david-marx/ Credits: This episode was produced by Ben Brock Johnson and Amory Sivertson. Production assistance from Grace Tatter. Mix and sound design by Paul Vaitkus. It was co-hosted by Ben Brock Johnson and Amory Sivertson.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Support for WBUR comes from the Quiet Tension Podcast. When Joe Missoula got the Celtics job, Steve Paliuka sat up until 1:00 in the morning typing him 25 things about leadership. Dr. Sharon Turbin asks what came first on the list. Listen closely wherever you get your podcasts.

• 0:19Speaker 01

  Support for Endless Thread comes from MathWorks, creator of MATLAB and Simulink software to design and develop engineered systems, accelerating the pace of discovery in engineering and science. Learn more at mathworks.com.

• 0:34Speaker 02

  Ugh, I hate Mondays.

• 0:36Speaker 03

  King's Hawaiian cinnamon swirl bite?

• 0:37Speaker 02

  Uh, Taylor Hansen? Sure, I'll try one. Mmm.

• 0:43Speaker 04

  Hey, let's get back to work, please.

• 0:45Speaker 02

  But Taylor Hansen's making my day way better with these new soft and swirly King's Hawaiian cinnamon bites.

• 0:49Speaker 04

  Taylor Hansen? Nice. Try one. Mmm.

• 0:56Speaker 05

  King's Hawaiian cinnamon bites. There's nothing like it.

• 1:05Speaker 00

  WBUR Podcasts, Boston.

• 1:12Amory Sivertson?

  Derek, do you remember if there was a particular moment in time that you realized that you had an eye for style or fashion or however you think of it? Like, do you remember how old you were?

• 1:27Speaker 07

  No.

• 1:28Amory Sivertson?

  And what you were seeing?

• 1:29Speaker 07

  No, there was not a Tom Ford moment where I thought, I have sophisticated taste. No.

• 1:35Ben Brock Johnson?

  You took one strap of your ash-kash-bagash, uh...

• 1:39Speaker 07

  Yeah, no.

• 1:40Ben Brock Johnson?

  ...off and let it down, and then you knew. That's when you knew.

• 1:45Amory Sivertson?

  Derek Guy, the menswear guy, doesn't really know how it started. It seems to have started on various internet forums devoted to discussions of fashion and style.

• 1:56Ben Brock Johnson?

  How's it going? Well, you don't have to look far on Reddit or Twitter to find discussions around fashion that discuss or are driven by Derek. And maybe that's because he's pithy and snarky and extremely online whilst discussing highfalutin topics with some balance.

• 2:18Speaker 07

  So there are some people who think that there is some objective truth in fashion, that this is a better look and that's a bad look. And there are some people who view it as completely subjective, that, you know, well, I just put on whatever makes me feel good or what I think looks good. And everything's legitimate. Everything that anyone chooses is totally fine.

• 2:36Amory Sivertson?

  Oh, thank goodness. We're all our own special mannequin.

• 2:40Ben Brock Johnson?

  But you best come correct, mannequins, and be thoughtful in your presentation.

• 2:45Speaker 07

  I think of dress as a kind of cultural language. And just as we use, you know, spoken language right now. And I think there is a certain way that you can dress that is not necessarily about pure subjectivity or objectivity, but is about whether or not someone is adept at using cultural language. Are they able to communicate something that makes sense to other people around them that expresses something about their identity, whether it's about their gender, sexuality, whether it's about culture? At least for me, I think, once you think of dress as cultural language, it then becomes a lot easier so that you're not stuck in these kind of questions of, does black go with blue?

• 3:26Amory Sivertson?

  But does it, Derek? Does it?

• 3:29Ben Brock Johnson?

  The reason we ask is, again, because Derek really is now the go-to internet critic of men's fashion. Whether it's a particular blazer on a political figure, the wardrobes of semi-fictional characters in HBO's hit Succession, or how to score Grant Stone penny loafers on eBay, Derek Guy is the guy.

• 3:51Amory Sivertson?

  And who loves tweed and pleats and wanted to talk to him? This guy.

• 3:56Ben Brock Johnson?

  And this gal.

• 4:00Ben Brock Johnson?

  I'm Ben Brock Johnson.

• 4:02Amory Sivertson?

  I'm Anne Marie Sivertson, and you're listening to Endless Thread.

• 4:06Ben Brock Johnson?

  We're coming to you from WBUR, Boston's NPR.

• 4:09Amory Sivertson?

  Today's episode, Derek Guy, who may have only talked to us because he thinks Endless Thread is a fashion podcast. We're not really sure.

• 4:20Ben Brock Johnson?

  We'll set him straight.

• 4:30Amory Sivertson?

  So your blog and your social media handle are Die Workwear. How do you define workwear? Can you put a visual on it for us?

• 4:39Speaker 07

  Oh, Lord.

• 4:40Amory Sivertson?

  And why must it die, Derek?

• 4:42Speaker 07

  Okay, so I started that blog in 2011 on Tumblr. And I put literally like two seconds into the idea. I mean, it's like, you know, whenever you sign up for a social media site, you just, you have to type in something and like, no, at least not me. I didn't like, think of like, oh, I'm going to start this blog and it's going to grow. And I'm gonna, you know, like a mass of 1 million following on Twitter. Like I just, at this point, like, I can't change the name. Imagine if you named your blog, you know, Poopy McPoop. And then all of a sudden, for the next 15 years, people are asking you, what does Poopy McPoop mean?

• 5:21Amory Sivertson?

  Oh, I'm so sorry.

• 5:22Speaker 07

  And you had no, you had no idea.

• 5:26Ben Brock Johnson?

  Derek's love for clothing started before he was making jokes on his Tumblr about city hipsters wearing lumberjack and dock worker outfits. And while over time, he's become an official critic, cited or published in various magazines for his takes on menswear. Derek really does think about style and fashion as a form of communication, which made a lot of sense to us. It's nuanced, right?

• 5:51Amory Sivertson?

  But that doesn't mean Derek is allergic to a strong opinion or a hot take. In fact, if you ask him how he became the subject of Reddit threads, magazine articles and retweets galore, he would point to a moment when he put some strong feelings into the world.

• 6:07Ben Brock Johnson?

  On where else? X, or as we called it in 2022, and some of us still call it this, Twitter.

• 6:14Speaker 07

  October of 2022, I believe, I had around 50,000 followers. And at the end of October 2022, Dave Portnoy, who's the founder of Barstool Sports, announced that he had founded another company called Brick Watch. And this was a company where he was trying to sell watches for, I think, around like $2,500. And they were made in America and he described them as basically the same as Rolex, but you could get it for, you know, something like roughly like a tenth of the price or so. And I took a look at the company and I saw that one of the watches, one of the watches had a mechanical movement, the other watch had a quartz movement.

• 6:55Speaker 07

  And quartz for, you know, for like people who are into watches is basically a battery operated movement. And I went to Twitter and I said, this is a ripoff. I wouldn't even sell this to my enemies. I couldn't imagine selling it to people who support me. And I said, this is made with, this is a $40 watch. What I should have said, and I misspoke, is that it was made with what a $40 quartz movement because you could, you could buy that Rhonda quartz movement for about $40 from any kind of watch repair shop. And that tweet went kind of viral and then Dave Portnoy made a video in response, which I couldn't believe.

• 7:38Speaker 07

  And then a bunch of his fans piled into my comment section and said, well, how is this different from what Ralph Lauren does? Ralph Lauren buys $50 cashmere sweaters and he sells them for 500. So I screenshotted that person's reply. And you have to know that up to this point, I had been on Twitter for about 11 years. And throughout that entire period, amassing this follower of like 50,000 people, I was speaking to other menswear nerds. So I would be purely making self-deprecating jokes about our own obsessions.

• 8:09Ben Brock Johnson?

  Yes.

• 8:09Speaker 07

  And that, when I screenshot that tweet, that was the first time, one, I did a thread where you link a bunch of tweets together to form a story. And then two, I broke out of quote unquote, character because, you know, at the time I was just making self-deprecating jokes. And then now it's like doing a serious thread. I said, well, actually the, it doesn't, there is a story of how cashmere comes to the market and buying cheap cashmere is bad. And here's how you find a good cashmere sweater.

• 8:40Ben Brock Johnson?

  You did a well actually, but it was a good well actually.

• 8:45Speaker 07

  So that went up in beginning of November, I believe, of 2022. And that went viral. And then a bunch of journalists contacted me, like the Washington Post contacted me and some other kind of publications. And then by the end of that year, my count had gone up to about 100,000 followers.

• 9:04Ben Brock Johnson?

  Quickly doubling his followers on Twitter may have been the result of Derek's Barstool Sports Guy Bad Watch takedown. But he has another floating theory about something else that may have played a role in helping the menswear guys' online community pop off. In 2023, Twitter also instituted its FYP, For You page. And Derek had just gotten a lot of interaction on the platform for his critical thoughts on watches and sweaters.

• 9:32Speaker 07

  My guess, and I don't know for sure, although some people high up in Twitter have reached out to me for like clothing advice. And I've always wondered, like, should I ask this person, like, what went on in the code?

• 9:46Amory Sivertson?

  Yes.

• 9:47Speaker 07

  But I haven't, I haven't asked. But my guess is that when they instituted the For You algorithm, and this is only my guess, is that they had to base the algorithm on something. And since I had been going viral in November and December because of my back and forth with Dave Portnoy and then the Kashmir thread, that maybe they just coded the algorithm serve whatever was popular in the last two months. And it just happened to be me. And then.

• 10:18Ben Brock Johnson?

  That's some good timing, Derek.

• 10:19Speaker 07

  Yeah, that's what I think happened, but I don't know for sure.

• 10:23Amory Sivertson?

  I don't know for sure either. But this For You page episode in 2023 is definitely how I first found Derek. Because, believe it or not, Ben, I was not following menswear. It's not my usual jam. But a thoughtful, well-researched Twitter takedown thread, that very much is my jam. And Derek can deliver in that department. Take, for example, a recent thread about a Saint Laurent wallet that, according to Dave. Derek's analysis is machine sewn instead of hand sewn and made to look more expensive than it really should be.

• 11:02Amory Sivertson?

  Or another on Pete Hegseth's fashion choices, explaining the time and place for a light-colored shoe and sock. Spoiler alert, our defense secretary, wrong time, wrong place, Derek says.

• 11:16Ben Brock Johnson?

  He does have rules of engagement, though. Don't sweep the digital legs out from under regular Joes.

• 11:22Speaker 07

  I would never pull a random person's photo off of Instagram and blast it to... I wouldn't even do... I didn't even do that even when I had 50,000 followers. I definitely wouldn't do it when now I have over a million followers. Because, you know, like, someone's just trying to get dressed. Like, you're just putting them on blast. To me, it's a crazy thing. So I try to only criticize famous people. And then, if I have to pull from famous people, I have to choose somebody. So I tend to choose people who, I'll be honest, I feel less sympathy for. So I'm more likely to use the photo of, like, Matt Gaetz or Jordan Peterson than I am, you know, of some random person. It can get kind of political at times because people will notice, like, oh, you're constantly using Matt Gaetz's photo.

• 12:06Speaker 07

  And yeah, because he's widely photographed. There are a lot of photos of him. He often demonstrates something that I think is bad with tailoring. And then he also has gone on record saying that people should be offended and you shouldn't hold back. So, okay. Like, you know? And my other feeling is that even if it's a famous person, I would never... whatever their politics or their beliefs or whether they've... whatever they are, I would never criticize a young person. For me, like, even... Sometimes people, like, send me images and say, can you say something about Baron Trump? I think sometimes he actually looks pretty good in his clothes, depending on the outfit. Like, Mitch McConnell wears dress sneakers, which is an item that I don't think looks very good.

• 12:51Speaker 07

  But, you know, like, he's also taken falls. And he's older. So, like, I don't know. Like, just have some common sense, you know? Like, you're not gonna put an 80-year-old... I don't know how old Mitch McConnell is. But, you know, if he's 80, let's say. I'm not gonna put an 80-year-old man's photo up and say, like, look at these stupid shoes or, like, you know, put an 18-year-old and say, look at these dumb pants. That's a crazy thing to do.

• 13:21Ben Brock Johnson?

  Baron Trump, Mitch McConnell, it is true that, well, we live in a time when everything feels like a political statement. And while Derek does try to steer clear of politics, he says in his regular fashion tweets, some of his posts do seem to suggest that Derek is, you know, a little deeper than the lapels on his jacket. And he does post about hot button issues with some regularity, like a recent tweet over whether someone who's in the US illegally can legally receive a social security number from the federal government.

• 13:57Amory Sivertson?

  And you bet this one person who told you basically to, you know, stay in your lane, that if you could prove this to be the case, that you can legally get a social security number, that they would have to donate $5,000 to a particular cat rescue that you support. And if you are wrong, you would donate $5,000 to a charity of that person's choice. And then you open the bet to anyone. What made you want to put a bet like this on the table, given that it's not the main focus of your content usually?

• 14:32Speaker 07

  Yeah, I mean, there are a lot of things that are important to me. I don't have an algorithm of when I say something. Immigration is a particularly touchy subject for me. And then, I, I don't know, you know, some, I don't know, just like anybody, I'm literally like anybody else. I don't know what is going to end up going viral. You know, sometimes some tweet gets, you know, a lot of likes, sometimes a tweet doesn't. That one happened to get a lot. And then there was news that ICE is going to, or the IRS is going to cooperate with ICE and give them tax information so that ICE can go and deport these people. I don't know what to say besides I... Feel bad for people in those situations.

• 15:17Speaker 07

  And so I made a, you know, I, a bad habit of mine. I mean, the, the good gentlemanly thing to do is to be earnest and say something very respectfully and all that. But I am a very snarky person. So I said, how can this happen? I was told that immigrants don't pay, illegal immigrants don't pay taxes. And then a bunch of people piled in and said they, you know, they don't pay taxes or they don't, they have illegal social security numbers. I, I know that illegal immigrants can legally get social security numbers. For example, Dreamers, people who were brought here as children and then they grew up here and through the Obama administration were given deferred action that they would not be deported if they came out of the shadows.

• 15:59Speaker 07

  Through that process, they were able to get a social security number and then they paid taxes. So I don't, you know, I, I said something snarky and then a bunch of people piled in and I said, well, why don't we make something good out of it? If you really believe this, let's put a wager. And if I can raise 5,000, 10,000, 15,000 for a cat charity, sure, like we'll make a spectacle of it. And if, if, and if I'm wrong and you prove to be right, I'd be happy to donate to a charity.

• 16:24Amory Sivertson?

  What's the status of this bet at the moment?

• 16:28Speaker 07

  Uh, some people said, I'll take you up on it. And I DM them. Uh, there are three people who said, I'll take you up on it. Of the three people, two people had their DMs open and I DM them. I said, okay, um, here are my terms. Here's what I define as an illegal immigrant and here's, I, I basically gave the terms and I said, I would like for both of us to send 5,000 to a trusted intermediary so that, that they can handle the distribution once this is done. No one can back out and then I'm waiting for them to reply. You know, there's, there are a bunch of important issues. Immigration is not the only important issue in the world.

• 17:06Ben Brock Johnson?

  Derek, let me, can I just ask you, how, how come it, it feels so important to you? I'm, I'm curious to understand more. I mean, I, I'm hearing everything you're saying and it, it makes sense to me, but it seems to come from a personal place.

• 17:21Speaker 07

  I, I'm a child of immigrants. I grew up in an immigrant community. If, if you're interested in fashion, the way that I am, and you go to garment factories, you know that these garment factories are staffed with both legal and illegal immigrants.

• 17:34Ben Brock Johnson?

  So it pisses you off when people say that immigrants are like not working or not doing their fair share or not contributing to society?

• 17:44Speaker 07

  Listen, I am a pragmatist. I know that a country has to have borders and that, you know, people in there are going to enforce, you know, immigration rules and all that. I understand all that. I'm just telling you, in my heart, when I'm moving through the world, I feel for people who have to live in the shadows and have to go through life worried about any kind of, not even federal agents, but state agents, police approaching them. Some of these people, again, came here as babies. They may not even speak the language of their parents' home country. They may not know the customs. Like, you're seen as an American, because you are an American. You grew up here.

• 18:25Ben Brock Johnson?

  Yep.

• 18:26Speaker 07

  So, you know, I don't know what the solution is. I'm not, while I am sympathetic to all immigrants, both legal and illegal, I understand that practically as a political matter, that is not a winning message to say, just open the borders and let anyone come through. I understand there has to be screening. I understand that some people broke laws and they came in here. Mike Davis wrote this, has done brilliant work on cataloging the labor movement

• 18:53Ben Brock Johnson?

  Yeah.

• 18:54Speaker 07

  across the US and especially Southern California. And I understand that, you know, when companies, when companies kind of like took in all these immigrants, they use that sometimes for union busting. I understand all of those issues. And I don't want to pretend that all of these immigrants are from Latin America. There are actually a lot of illegal immigrants. They're not Latino. So, the story's much more complicated. But I feel for anyone who migrated, as my family did, from Vietnam after the war, or during the war, when their city was being bombed, that they fled from Vietnam to Cambodia, to Iran, to Canada, and then the United States. I feel...

• 19:34Speaker 07

  I understand that pain.

• 19:35Ben Brock Johnson?

  Yeah.

• 19:37Ben Brock Johnson?

  And when you say Mike Davis, you're talking about the author of City of Courts and.

• 19:41Speaker 07

  Yes.

• 19:41Ben Brock Johnson?

  Yeah.

• 19:42Speaker 07

  Yeah. I, I, I, I understand all of the complaints. I'm just saying that I don't know what. I don't know what to say, you know, like when my parents' city was being bombed, I don't, I don't know. You, you want them to sit there and be bombed? I don't know, but you know, I, when I say that online, people say you're an immigrant, you have no, you have no right to say what goes on in this country. Oh, fine. I, you know, just expressing my opinion on another platform.

• 20:08Ben Brock Johnson?

  Yeah.

• 20:09Speaker 07

  You know, I'm just a guy who built a platform.

• 20:11Ben Brock Johnson?

  How dare you express your opinion on Twitter? That's ridiculous. How dare you, sir?

• 20:14Speaker 07

  Yeah.

• 20:16Amory Sivertson?

  Coming up, more opinions from Derek and more history, including the metrosexual origins of manospheric fashion? Yep, that's in a minute.

• 20:47Speaker 00

  Support for WBUR comes from the Quiet Tension Podcast. There's a part of high performance that drives you, shapes you, and pulls at you too. Rarely spoken, almost never examined, that's the quiet tension. Coming up, psychologist and executive coach Dr. Sharon Turbin with Steve Paliuka on what separates the leaders people follow from the ones they don't. Stay with us for a preview. Listen closely wherever you get your podcasts.

• 21:16Speaker 02

  Ugh, I hate Mondays.

• 21:18Speaker 03

  King's Hawaiian cinnamon swirl bite?

• 21:19Speaker 02

  Uh, Taylor Hansen? Sure, I'll try one. Mmm.

• 21:25Speaker 04

  Hey, let's get back to work, please.

• 21:26Speaker 02

  But Taylor Hansen's making my day way better with these new soft and swirly King's Hawaiian cinnamon bites.

• 21:31Speaker 04

  Taylor Hansen? Nice.

• 21:33Speaker 03

  Try one.

• 21:35Speaker 05

  Kings Hawaiian cinnamon bites. There's nothing like it.

• 21:46Speaker 09

  I'm Alison Aubrey, longtime health and science correspondent with NPR. And I've got a new podcast all about the science and wisdom of life after 50. It's called Your Turn with Alison Aubrey. We want to take you on a journey to help you explore all the opportunities to make change and feel good as you step into middle aged and beyond from WBUR and NPR.

• 22:11Ben Brock Johnson?

  Your Turn with Alison Aubrey from NPR and WBUR. Supported by AARP. New episodes every Thursday.

• 22:23Amory Sivertson?

  All right, we've been talking to big on Twitter menswear aficionado Derek Guy, who, as you may have guessed by now, is not the middle aged white guy with glasses and a side part his online avatar might lead you to believe. That is of a fashion icon of Derek's, who is not trying to be a fashion icon at all.

• 22:43Speaker 07

  There's this guy named Elliot Richardson, who worked in the Nixon administration, who I think was just beautifully dressed. And he wore the hallmarks of that classic American look. The shape of the shoulders, the construction of the waist, the types of ties that he wore, the way that he wore his tie knot, the way that he dressed so perfectly encapsulates what I think is beautiful, a classic American tailoring.

• 23:08Amory Sivertson?

  And as you also might have noticed by now, a conversation with Derek about fashion is also a conversation about history. Take, for example, a recent thread of his that started as a discussion of the perfect suit for the writer Gary Steingart and turned into a lesson about classic American tailoring and lapel buttonholes and the silk weaving skills of the Huguenots. A Derek Guy thread isn't so much about what's right or wrong in fashion. It's about where specific aesthetic choices come from.

• 23:40Speaker 07

  I want to write stories about like 1970s hikers and Soldiers in this war and like, how did these, how did these people dress? And how did it affect how we dress today? You know, I recently wrote an article for Bloomberg about the creation of alpha male aesthetic, which is like basically how Andrew Tate dresses. He's a bit more extreme, but there's a lot of like really muscled guys wearing these really tight suits and so it's like driving expensive cars and so on and so forth. So I wrote this article for Bloomberg and to me, a really amazing thing about that look is that you can, I will say, getting back to that, that editor reached out to me and said, can you do 2,000 words on this, the creation of the alpha male aesthetic?

• 24:23Speaker 07

  I submitted 3,700 words because I wanted to start at the story of the industrial revolution.

• 24:31Speaker 07

  And I said, like, when they're trimming this down, which I, I could not praise my editors enough for their patience and skills, and they've trimmed it down quite a bit. But as they were trying to cut, I was like, no, I really need to talk about, you know, the outdoorsman in like the late, you know, like 19th century.

• 24:49Speaker 07

  So I think when you use clothes in this way and you see something, often if you just tug at, you know, not to make too corny of analogy, but if you tug at the yarn a little bit, you'll find out that there's this like amazing history that connects you to all of this cultural history of, you know, like, why are his pants that tight? Well, it goes back to what I think is this early 2000s history of the, the rise of the metrosexual. Why does he, you know, body build in this way? Well, it goes back to the 1970s and the, during the industrial revolution, how we started to think of muscle culture and so on and so forth. I think when you think of aesthetics in this way, you can get at issues that a lot

• 25:33Speaker 07

  of people are interested in, which are ideas of politics, economics, community, identity, society, culture. And so it's not just random trends. You know, the way that we dress is often a reflection of, you know, the, the kind of spirit of our age. And that is, the spirit of our age is very much shaped by politics and economics and and whatnot, these larger forces.

• 25:59Ben Brock Johnson?

  Derek points out that in the early 1800s, because of the Romanticism movement, the Western European standard for male beauty was specifically that you did not look like you ever worked out a day in your life. You were a melancholy, romantic gentleman.

• 26:17Amory Sivertson?

  This was the ideal male body. Pasty and pudgy is what peak performance looked like. And then the Industrial Revolution and the age of the machine changed that. As did the 1970s and feminism and the reaction to feminism and on and on. So even though Andrew Tate and other drivers of the manosphere might say that an incredibly tight-fitting suit is, quote unquote, "traditionally male."

• 26:45Speaker 07

  In my view, it's not necessarily traditional. It's really shaped by the last 20 years of culture wars, although it pulls from earlier movements selectively. And I think that is just a reaction to

• 26:59Speaker 07

  discussions that we have of trans rights. And then from that, discussions of whether or not there is such thing as gender as performance. And in my view, what Andrew Tate is doing is essentially performing his view of gender.

• 27:20Ben Brock Johnson?

  Do you like movies? Is there like a specific movie that to you has like a fashion or style language that is like delicious?

• 27:33Speaker 07

  Well, the corny, there are two corny answers, but...

• 27:37Ben Brock Johnson?

  Corny, I'm down for corny, whatever you want.

• 27:40Speaker 07

  Okay, the corny, the corny and obvious answer is Talented Mr. Ripley. Everyone, anyone who's into like men's style is going to say Talented Mr. Ripley. That's like the super obvious one. If you look at that film, you'll hear names like Baddestoni, which is this famous tailoring shop in Italy. You'll see like really classic, both American and Italian tailoring, beautiful proportions, really good casual looks as well. Not, it's not just suits and sport coats. You could see like, you know, just like really cool retro nets. And then the other obvious answer is any film with like Fred Astaire, Cary Grant, Gary Cooper. When you look at those films, especially Fred Astaire, that man is like...

• 28:23Speaker 07

  Twirling in the air and his suit is always staying exactly, it's color hugs the neck, beautiful form. And it's like, it's just incredible. If you, if you, if you really get into tailoring, you look at his films, it's incredible. Gary Cooper, same thing. Like you look at the way Gary Cooper dressed, Cary Grant, I mean, they're all really cliche answers. But really, when you see those films, you're like, wow, that looks fantastic. I do think that sometimes people say like, how, are there any books that you recommend for how to dress? And one, if you're talking about tailored clothing, just go back to those old black and white films. You don't have to dress like a 1940s detective if you don't want to. I, you know, I, I don't think you have to look like, you know,

• 29:07Speaker 07

  like one of those detectives that's flipping a coin in the air. But you'll get a sense of fit and proportion that you can translate into a more modern context.

• 29:21Amory Sivertson?

  Of course, that more modern context is very different from the monoculture of Fred Astaire and Gary Cooper. So does Derek feel any loss about that change? In classic form, he's mixed, and he has some further reading to suggest.

• 29:38Speaker 07

  When I started following Menziger on the internet, it went from forums and blogs to now social media like Instagram and X. And then now I think we're in this other phase where a lot of content is now migrating to private Discord forums and paid Substacks.

• 29:56Speaker 04

  Yeah.

• 29:57Speaker 07

  I think that is, has, is not good. I think forums and blogs offered something unique, one, exchange of ideas between equally nerdy kind of people. You know, if you're wondering how to, I don't know, buy a suit or something, you could stumble upon a blog by Googling. It wouldn't be like hidden behind a Discord channel or a Slack server or paid Substack. And then I I sort of feel that social media is a very superficial form. You know, I do these long threads, but Twitter only allows you reasonably to only string together 20 tweets into a thread. If you took, if you copy and paste all of the text and put them into a Word document, it'd be like, I don't know, like maybe half a page.

• 30:42Speaker 07

  That's nothing. That that's like, that's like a normal post on a forum.

• 30:47Ben Brock Johnson?

  Even 500 words.

• 30:47Speaker 07

  And it's maybe one three hundredth of a book. So, you know, again, I think the internet's pretty neutral. It's like how you end up using it. The internet can be great if you use it well. I do think that some of the trends are not great. And I feel that the forums and blog days were better than where we were, where we are now.

• 31:09Ben Brock Johnson?

  Well, you, you, earlier, you talked about this idea of like monoculture, right? The internet has also helped to bring around, bring about a death of monoculture in a way. And there are some good things about that, right? When it comes to fashion and style?

• 31:25Speaker 07

  Yeah, you know, really good for, for your listeners, if they want to look up the essay, Kathy Horn, C A T H Y and then H O R Y N. She wrote an article, I believe for Times, the New York Times Magazine. And it's called The End of Trends. And her thesis was that essentially so much of our culture is now online. And that it's no longer the case that, that Vogue editors and GQ editors are dictating fashion. People can participate in online fashion conversations. And that people are essentially curating their own feeds. And they exist in different kind of cultural communities.

• 32:06Speaker 07

  So that microtrends, you know, kind of exist in these small communities and they don't necessarily seep into other communities. And this diversity of culture online means that we've reached the end of hegemonic trends that were in the 1960s, you can say like, this was a look. In the 1970s, there was a look, in the 1980s, 90s. But since then, a friend of mine who wrote a really wonderful book. Called Culture and Status. It might be called Culture and Status or Status and Culture. I always forget. But his name is David Marx, M A R X, same as Karl Marx. But his name is David Marx. His book is about how we we create culture by pursuing status. And one thing that he said to me once is that if you go back and look at old episodes of Friends,

• 32:50Speaker 07

  you know, Friends was in the 90s and they kind of dress like how people do today. There's like small differences, but it hasn't changed that much. And that there are all of these other communities that then have their own distinct kind of style, subcultures, and they have not necessarily taken over all of culture. And the general zeitgeist has kind of been the same. So it's one kind of monoculture in the sense that we don't have these like constant moves of like 60s, 70s, 80s style shifts. But it's also that it's much more diverse, that there are smaller things that don't necessarily take over everything, but we all exist in these small communities. And I agree, that is generally a good thing. There is more diversity. I always think that I do believe that the best time in fashion and culture is today.

• 33:35Amory Sivertson?

  If you were a cartoon character, Derek, and you had to wear the same outfit every day for the rest of your life, what would it be?

• 33:46Speaker 07

  Again, super corny. I can't I can't escape my corniness. But if I had to choose, be a brown tweed jacket, tanned whipcord trousers, black tassel loafers, black calf skin tassel loafers, and a light blue Oxford button down shirt.

• 34:05Speaker 07

  You know, I was asking for watch recommendations from a friend who collects watches. He gave me this recommendation. He said, that's kind of like a more intellectual watch. And I think what he meant was that you're a nerd. And I thought it was funny because there are sometimes, as we all do, we buy clothes because we aspire to be a certain figure. So there are like things in my wardrobe I buy. I was like, oh, I'm gonna be a tough guy. And I'm gonna buy, you know, this like leather jacket or whatever. But I recognize that like in my heart of hearts, like I feel most comfortable as a nerd. And I am a nerd and people see me as a nerd and like it's very transparent. So that probably would be what I would wear for the rest of my life.

• 34:44Amory Sivertson?

  Nerdy seemed like the most appropriate place to end. An important word in our cultural language.

• 34:51Ben Brock Johnson?

  Emery, what is your favorite menswear outfit to wear yourself or see on a man or person of any gender?

• 35:02Amory Sivertson?

  I don't know. I've got a good vest. I like a good, a good dress vest. That you can wear just as a vest.

• 35:11Ben Brock Johnson?

  You mean like a, like with a, with a hole for a pocket watch? Like that kind of vest?

• 35:16Amory Sivertson?

  Not quite that fancy, but just like

• 35:18Ben Brock Johnson?

  A waistcoat?

• 35:19Amory Sivertson?

  A shirtless vest situation. We do not need a shirt. We just need a vest, you know?

• 35:24Ben Brock Johnson?

  That's it? Just a vest?

• 35:28Ben Brock Johnson?

  Just Donald Duck in a vest? Is that what you're suggesting?

• 35:33Amory Sivertson?

  Yeah, and a monocle, just for good measure.

• 35:36Ben Brock Johnson?

  A vest and a monocle, nothing else?

• 35:46Ben Brock Johnson?

  All right.

• 35:47Amory Sivertson?

  What about you?

• 35:49Ben Brock Johnson?

  I don't think I could top that, to be honest. I feel very, uh, no, I

• 35:56Amory Sivertson?

  All right.

• 35:58Ben Brock Johnson?

  I think I love a, I have, I will say that like, I was very skeptical of athleisure. But I think there is a way to do it stylishly. I mean, this is an obvious statement, but like I, recently I've been like some really nice cushy sneakers. And like a, a, a pair of pants that are, you know, that are, um, that have some elastic in all the right places. But also like cut a nice shape, you know, for the legs. A sort of technical sweatshirt or like a very plush hoodie.

• 36:39Ben Brock Johnson?

  And, and a ball cap, and a square ball cap.

• 36:42Amory Sivertson?

  And just throw in a monocle for good measure.

• 36:44Ben Brock Johnson?

  Yeah, and a mon, you know what?

• 36:46Amory Sivertson?

  Athleisure and a monocle.

• 36:49Ben Brock Johnson?

  Throw on a monocle. All right. I'm in. I'm in.

• 37:05Ben Brock Johnson?

  This episode was written by me, Ben Brock Johnson, and produced by me and Amory Sivertson with production assistance from Grace Tatter. It was co-hosted by me and...

• 37:15Amory Sivertson?

  Me, Amory Sivertson. It was mixed and sound designed by our production manager, Paul Vikes, and edited by Meg Kramer.

• 37:22Ben Brock Johnson?

  The rest of our team is Franny Monahan, Dean Russell, Emily Jankowski, and our managing producer, Suma Tajoshi.

• 37:28Amory Sivertson?

  Endless Thread is a show about the blurred lines between online communities and athleisure with a vest and a monocle.

• 37:35Ben Brock Johnson?

  If you have an untold history, an unsolved mystery, or another wild story from the internet that you want us to tell, hit us up, [email protected].

• 38:01Speaker 00

  Support for WBUR comes from the Quiet Tension Podcast with Dr. Sharon Cherben, psychologist, executive coach, and a close listener to what lives beneath high performance. Here she is with Steve Paliuka, who built Bain Capital and helped bring a championship back to Boston on the thing the best leaders do that most don't.

• 38:22Speaker 10

  The best leaders kind of give credit and take blame. When something goes wrong, they're the first ones to take responsibility for it. And they see the good in the other people on the team. They don't immediately try to deflect whatever problem there was, what went wrong. You miss the sales target on the salesperson, they reflect on themselves and what they could do better. Same thing, you know, what Joe Mazzulla does in basketball. If you see his press conferences and the Celtics don't play well, the first thing he says is, you know, I need to coach better. I made a mistake here. I made a mistake there. Not many coaches do that. But that's why the players love Joe, and that's why, another reason, he's a great coach. So there are things like that that you learn. There are many, many more things like that I learned

• 39:05Speaker 10

  from people like Red Auerbach and my classmates from business school and sports and all the rest.

• 39:12Speaker 11

  And really, what an array of leaders, because leadership is both the same and different depending on the environment that you're in.

• 39:22Speaker 00

  Listen for more of the quiet tension wherever you get your podcasts.

• 39:27Speaker 02

  Ugh, I hate Mondays.

• 39:29Speaker 03

  King's Hawaiian cinnamon swirl bite?

• 39:30Speaker 02

  Uh, Taylor Hansen? Sure, I'll try one.

• 39:33Speaker 03

  Mmm.

• 39:36Speaker 04

  Hey, let's get back to work, please.

• 39:38Speaker 02

  But Taylor Hansen's making my day way better with these new soft and swirly King's Hawaiian cinnamon bites.

• 39:42Speaker 04

  Taylor Hansen? Nice.

• 39:44Speaker 03

  Try one.

• 39:45Speaker 04

  Mmm.

• 39:49Speaker 05

  King's Hawaiian cinnamon bites. There's nothing like it.