Alison Stewart: This is All Of It on WNYC. I'm Alison Stewart. If you spent any time on the social platform formerly known as Twitter in the last couple of years, you'll know my next guest as the menswear guy who posts comprehensive and informative threads about the history of men's fashion. Derek Guy has more than a million followers online who flock to him with questions about the best suit brands, how a jacket should fit, and the difference between a suit and a sports coat. He's here now to take your calls. Derek, welcome.

Derek Guy: Hi. Thanks so much for having me on.

Alison Stewart: We're excited. Listeners, tell us your menswear questions. Do you have a question about fashion history? Are you wondering how to dress stylishly for the winter or for some upcoming event? Are you trying to figure out what to buy for someone else? Give us a call. 212-433-9692, 212-433-WNYC. It's your chance to ask the menswear guy your question or you can send us a message @AllOfItWNYC. You started this GQ article that was written about you. You said that in high school, you started to realize fashion was important to you. Why was it something you cared about?

Derek Guy: I think that was true for a lot of people. My interest wasn't specifically in clothes, but clothes was part of a subcultural uniform. I was really into music at the time and went to dance clubs. I think if you're part of any scene, you get a sense that there is a kind of uniform for that scene. I think many people develop an interest in clothes through that kind of an interest in something else, so same thing happened for me.

Alison Stewart: Well, who were your personal heroes or influences when it came to men's fashion or maybe from music to men's fashion? [chuckles]

Derek Guy: Well, they were all kind of dancers in this burgeoning underground scene called "freestyle dance." A lot of those guys were dressed head to toe in polo. I thought they were just the most stylish dudes in the scene. Through them, I got introduced to Ralph Lauren. When I went to Ralph Lauren's flagships, that's where I got introduced to tweed jackets and chambray shirts and Oxford button-downs.

Then over time, I soon learned that Ralph didn't invent those things. He borrowed the chambray from the US Navy and the button-down was originally from Brooks Brothers and the best tweed jackets were from Savile Row. I just fell into the rabbit hole of finding out all the original stuff and then, through that, eventually discovered menswear blogs and forums, and I think in the early 2000s, basically grew up on menswear blogs and forums, which is how I learned a lot about men's clothing.

Alison Stewart: Well, you joined Twitter back in 2011. When did you start to notice that you were getting more attention?

Derek Guy: [chuckles] That happened at the end of 2022. From 2011 to October of 2022, I was mainly making jokes for fellow menswear nerds.

Alison Stewart: [laughs]

Derek Guy: There were a lot of jokes about niche Japanese workwear brands and buying too many olive-colored jackets and things like that. The end of 2022, Dave Portnoy, he started a watch brand called Brick Watch. I criticized it. I thought it was not a very well-made watch and it wasn't worth the price that he was asking. One of his followers went into my thread and said, "Well, how's this different from Ralph Lauren buying a $50 cashmere sweater and selling it for $500?

I screenshotted that tweet and I did a thread and I said, "Well, here's a breakdown of the cashmere industry. Here's the development of cheap cashmere. Here's what cheap cashmere has done to Mongolia's environment and here's how to find good cashmere even if you're on a budget." That thread went viral. After that, I got phone calls from Washington Post journalists and people asking me for quotes for articles on how to find good cashmere sweaters.

I realized at that point from the end of October 2022 to the end of that year, my account grew from 50,000 followers to 100,000. Once it ballooned to that size, I felt like I couldn't make any more jokes about these Japanese workwear brands because it wouldn't land and it wouldn't make any sense. I continued to do more informative threads instead of these snarky in-group jokes. People seem to like that. Over time, just more people followed because I was doing these threads.

Alison Stewart: We're already getting calls for you. This is Reid from Brooklyn. Hi, Reid, thanks for calling All Of It. You're on with Derek.

Reid: Hi, Alison, longtime, longtime. Derek, being also a longtime fan. I have two questions. First, I'm a big thrift shop guy. I really like eBay. What I'll do is when I go to a thrift shop, I'll find a shirt that I like and then look for it on eBay with the same brand. Pierre Cardin is great for that. I'll be blowing up my own spot doing that, vintage L.L. Bean. I was wondering if you had any other recommendations for shopping on eBay. Second, I was wondering about what the research process is for when you eviscerate somebody on Twitter because it's my favorite thing to watch. Watching someone come for the king and they always miss. Thank you.

Derek Guy: Well, that's very kind. I am always surprised at the reactions I get on Twitter. I'm just tweeting. I can't explain any of the reaction. Whatever comes to my head, I'm just putting in a thread to explain an idea that's in my head. For eBay, are there certain things that you're shopping for?

Reid: You know how you can't really find a sweater. I've seen a lot of your threads about shopping for Shetland wool and stuff. That's been very helpful. Yes, a lot of sweaters. With pants, it's so hard because the fit's just going to be something that you have to try. Yes, definitely sweaters, vintage shirts. Any tips you have for those would be much appreciated.

Derek Guy: For sweaters, a really easy way to find a good sweater is-- it's no longer true that you can read quality off of a country of origin label. There are many, many quality garments now coming out of China just because people use those factories and they spec good sweaters. They ask for good sweaters. It used to be that the machinery there was not very good and people would just go there only to make cheap sweaters. Now, people are making high-end sweaters.

It is true that prior to, I would say, the 1990s, 1980s, most of the good knitwear was coming from Scotland, for example. A very easy way to find a good sweater is on eBay. You'd search for the fiber that you're looking for. You'd search for cashmere or lambswool or Shetland wool, merino maybe. You do in parentheses, Scotland, comma, Scottish. Do a search and then there's a checkbox for title and descriptions, and then click Search again. That will pull up all the listings for that sweater that was made in Scotland.

The reality is that in Scotland, many of those companies were chugging along with really good machinery, really skilled workforce. They simply did not update themselves very well. In Italy, for example, a lot of Italian production ran on being very fashionable, which sometimes just didn't age very well. Then in China or some other places, you have a mix of really high-quality sweaters that were made in modern times, but a lot of bad stuff that was made also in modern times, but also in historical times.

An easy way is just to search for a Scottish-made sweater and you'll find a lot of good knitwear that way as long as you double-check the measurements. Anytime you're buying online and certainly eBay, you want to check pit-to-pit measurement. Measure it and compare those measurements to items that are already in your closet. That way, you know whether or not it's going to have a chance of fitting.

Alison Stewart: We got a DM on Instagram that says about surgeon cuffs on blazers and suits, which they say could add a little extra pizzazz. They want to know why designers stopped using them.

Derek Guy: Well, I would argue it's the opposite. Designers actually started using them because consumers associate surgeon cuffs with quality. Let's explain what a surgeon cuff is. A surgeon cuff is on a suit jacket or sport coat. The buttonholes will be cut so that you can unbutton the buttons. Historically, that was done on custom suits so that, supposedly, who really knows? Supposedly, a surgeon could roll up his sleeves to wash his hands without ruining his suit jacket.

The thing is, is that, over time, people have started to associate that with quality. Marketers will be like, "Oh, well, this suit costs $1,000, but it has surgeon cuffs." You actually don't want surgeon cuffs on a ready-made suit. What you actually want is an unfinished cuff. That means that the sleeves don't have buttonholes cut yet and the buttons come in a little pouch that should be in the in-breast pocket. The reason is, is because when you are buying a jacket, oftentimes, the sleeve has to be adjusted in some way.

Maybe it might need to be lengthened. Maybe it needs to be shortened, but it should be adjusted in some way to show about a quarter inch of shirt cuff. If you already have punched the buttonholes, then you can only shorten the cuff so much before the last buttonhole is too close to the edge and then it looks weird or you can only let out the sleeve so much before you end up getting too much space. Yes, it's kind of an unfortunate development. There's really no reason that designers should be putting surgeon cuffs on a ready-to-wear suit, but they do it essentially to sell more garments.

Alison Stewart: Derek, you've compared menswear to fashion, to the language of fashion, I should say. Why is that a good analogy?

Derek Guy: I think many people approach the process of dressing in terms of following trends like a celebrity wore something. Now, I have to wear something or the trend is slim fit or the trend is very baggy fit, so I now have to conform to this, or they think of it in these pseudoscientific terms like, "Oh, does black go with blue," or "I am this body shape. How do I dress for this body shape?"

I don't think of dress in that sense. I think of dress in terms of cultural language. Going back to your first question. When I was into a certain music scene and going to dance clubs, there was a certain kind of look for that group. If you went to a punk show or if you went to the beach to watch surfers or if you went to a skate park, all of these different groups had their own subcultural language for dress.

If you think of style in those terms and think what are the cultural languages that I want to emulate that I think are good and fit my personality and identity, it's much easier to answer those questions of how should something fit and what colors go with what. I also think that's how we interact with clothing. Clothing is a way for us to identify ourselves with a group, but also express ourselves as individuals within that group. It's basically a kind of social language, the way that we use slang or communicate.

Alison Stewart: These are two different texts, but they go together nicely. The first one says, "I learned so much from Derek and relied on his posts and his blog when I was shopping for a suit for my wedding this summer. Thank you, menswear guy." Then the other text says, "Hey, Derek, any thoughts on high-end pre-owned suits versus less expensive off-the-rack new? Give us some suit advice."

Derek Guy: Absolutely. I think you can definitely buy a pre-owned suit. It's always better if you're shopping for that in person because there are certain dimensions to any garment. This is true for any garment. Whether you're buying leather jackets or shirts or sweaters, there are certain dimensions that will determine whether or not it fits you. A suit is cut in such a way that it's much less forgiving. Small issues such as shoulder pitch if your shoulders are pitched forward or if you stand with a very straight back, all of these things can affect whether or not the suit hangs well on you.

If you're shopping secondhand, it is better if you can shop in person at a secondhand store. An easy way to find better suits or better-made suits, frankly, is to find out where rich people donate clothes in your area. Often, those will be located in wealthy neighborhoods or sometimes they might be at charity shops that are benefiting some organization that rich people care about like the ballet company or the orchestra or whatever.

Sometimes churches in rich neighborhoods will have really nice donations. If you have to shop on eBay, then obviously check those measurements and make sure you can return easily. I would never get too hung up on brand names, especially since the market has so many diffusion lines. Generally speaking, if you see a garment made in America or England, historically, it will be of a higher quality, although, again, I don't think it's true anymore.

Alison Stewart: I'm talking to Derek Guy, the mastermind behind Die, Workwear! a.k.a., the menswear guy. We are taking your calls. Do you have a men's fashion or other style question? Give us a call. 212-433-WNYC, 212-433-9692. We'll have more, including a question about suit vests, after the break.

[music]

Alison Stewart: You are listening to All Of It on WNYC. I'm Alison Stewart. My guest is Derek Guy, the mastermind behind Die, Workwear! He's the menswear guy. We're talking fashion. Let's talk to Mike. Hi, Mike.

Mike: Good afternoon. How are you?

Alison Stewart: Doing well. What's your question?

Mike: On suits. When you have a suit vest, the very bottom button, I was always told, should remain open. Is that a hard-and-fast rule or what is the rule around suit vest?

Derek Guy: Yes, generally speaking, the bottom-most button should not be fastened. That does come from this kind of antiquated rule that supposedly a king long ago got fat and unbuttoned his button and all of his courtiers followed. It depends somewhat on how the vest is cut. Some garments are cut in such a way that you cannot button the last button without pulling the fronts. On certain vests, you can button the last button. Generally speaking, the last button should not be fastened.

Alison Stewart: I want to get to your Twitter handle and your blog name, Die, Workwear! What does that mean?

Derek Guy: Well, I started this blog in 2011 and I did not expect anyone to read it. It was just because in 2011, this heritage craze for workwear and everyone in the city is dressed like a lumberjack. I actually love and wear workwear, but I literally typed something into Tumblr, which was a Tumblr blog at the time. It was a friendly jab at a friend of mine who really loves workwear. I didn't think that the blog would grow. Now, I've been stuck for almost 15 years now with a really terrible name just because I didn't put any thought into it. That's basically the answer. I didn't think anyone would read the blog and it was just a friendly jab at a friend of mine.

Alison Stewart: Let's talk to Jerry from Forest Hills. Hi, Jerry, thank you so much for calling All Of It. What do you want to ask Derek?

Jerry: Yes, so I'm a 50-year-old male. I was wondering, what style advice would you give in terms of wearing jeans with shoes? How does he feel about that? Also, what cut and style would work best in terms of everyday casual wear?

Derek Guy: My feeling on any question on how to dress is always contextualized by what is the aesthetic that you're inspired by. Generally speaking, people who are asking like if you're inspired by hip-hop, then, obviously, you're-- if you're inspired by '90s hip-hop, then you're wearing really baggy jeans. If you're inspired by '70s punk, you're wearing very skinny jeans. Most often, if someone's asking this question, they're just getting their first steps into dressing better.

In that regard, I think a really easy cut is to wear a cut that's not overly slim, but it's a slim-ish straight leg. There's a cut called 19-- Well, it's a 1947 version of Levi's 501, which is not high-rise, but it's slightly higher-rise than many of the low-rise jeans that are popular at the moment. It's comfortable through the leg, but not baggy. It's a fairly straight fit with a slight taper. Those are sold through Levi's Vintage Clothing's subline, which can get very expensive, to be honest.

I want to say those are maybe $250 or $300, which is a big ask. A way around that is Gustin has a new fit called the 1968 Vintage Fit and it's pretty close to that cut. I think if you get that and then for button-up shirts if you're wearing it with jeans, consider a slightly more casual shirt. Instead of your dressy white poplin spread collared shirts, consider plaid flannel shirts or chamois shirts or a light-blue Oxford cloth button-down.

Anything with some texture or pattern is going to look a little bit less dressy than the stark pinpoint white poplin shirts that people wear to the office. In that sense, you're combining a slightly more casual item with another casual item, which is your jeans. Then obviously, for your shoes, I would, again, go for something-- That can be anywhere from chukka boots to sneakers to penny loafers.

Anything I would say, except for Oxfords. Oxfords are the lace-up, closed-facing shoe that you would wear with suits. Those, again, would be too dressy for the outfit. A very easy way to think of dress is just think of the ensemble that you're putting together and try to make everything coherent in terms of formality and social language. That's the really easy one-sentence advice that I'd have.

Alison Stewart: Let's talk to Eric in Bed-Stuy. Hi, Eric, thanks for calling All Of It. You're on with Derek.

Eric: Yes, thank you so much. Love the show. Derek, I'm a bigger guy. I'm about 6 foot 7. I just got my first suit a couple of years ago, custom-made, but I don't know a lot about suits. I invested a lot in it. It's really the only suit I have. For bigger people who need special sizing, what advice would you have for them when looking for a suit, especially if they don't have the money to go invest in a custom-made suit every time?

Derek Guy: This is a really difficult question for two reasons. The main reason is that the suiting industry has largely died to some degree. The US used to have thousands of tailors. There used to be a tailor in every town. That is no longer the case. The suits that you find often fit a very narrower scope of people. They come in a very limited number of fabrics because the store has to figure out how to make money to pay rent.

One way if you're a larger guy is to check out O'Connell's. It's a store in Buffalo, New York. They carry larger sizes. They will often draft a new paper pattern as they scale up into larger sizes. I have seen some people look pretty good. I know they have a very bad reputation, but I've seen some people look really good in Jos. A. Bank kind of suits. I think the most important thing is when you're trying on a garment to pay attention to the fit of the shoulders, the chest. Make sure that the collar hugs your neck. Make sure that the jacket, especially if you're 6'7", tries to, as best as you can, end about halfway from the back of your jacket's collar to the floor when you're in heeled shoes like dress shoes.

That is going to be a much more flattering fit. Then obviously, make sure that you can button the jacket without straining. Importantly, hug somebody like you can move comfortably without feeling like the back seam is going to rip. It's going to be hard if you're 6'7" and you're a larger guy. If you want a really good fit, that's generally the world of custom. We are unfortunately in a world where there just aren't very many good custom tailors. Custom tailoring is expensive, but I feel for people who I can't give a better answer to, but that's my answer.

Alison Stewart: It's great. You know what? I was on your feed and you point out that Matty Matheson from The Bear has great style.

Derek Guy: Yes, I think he has fantastic style. I think he's one of the best-dressed men right now as far as celebrities, I think most of the really stylish people are not celebrities. Among celebrities and also among non-celebrities, I think he's one of the best. I suspect his suits are custom-tailored, though. Yes, he probably gets custom tailor.

Alison Stewart: The question is, does black go with blue?

Derek Guy: Totally depends on the context. A black silk knit tie or a black grenadine tie looks fantastic with a navy suit. A navy suit or black Oxfords are a really natural accompaniment to navy suits because of the history of how London men used to dress for business. That's where we get most of our suit rules. Does a navy polo go with black jeans? Not really because there's no social history around that. It's not terrible, but it's like whatever.

For example, would navy shoes go with a black suit? No, because that's a weird thing to do. That's what I mean. When you think of ideas like this, you have to figure out, what is the context? What is the item? What is the social language that I'm operating in? You wouldn't wear navy shoes with a black suit because that's not something that's done. Just like you can't put in random letters into a word and expect it to still be the same word.

Alison Stewart: This is a great question. I hope we have time for it. "My question is regarding suit pants and the ankle specifically. How high should the ankle go? Should it show the shoe or cover the shoe? Can we show our ankle? I am mid-30s and my dad, who worked on Wall Street, is much older. We have very different view about this."

Derek Guy: Very, very dependent on the outfit that you're creating. There are certain outfits where it's fine to wear a slightly more cropped leg. There are certain outfits where it's actually fine to have a stacked leg like to have really long pants. Generally speaking, if someone's asking this question, they're asking about very basic outfits. In that sense, I think that you should stick to a very classic rule, which is the pants should either be a shivering break, which means that the hem just touches the top of your shoe, or it should have one break, which means there's just one break in that straight line from your hips to the top of your shoes.

When you're getting trousers hemmed, just wear the shoes that you would normally wear with the pants. You can ask for no break or shivering break or you can ask for a single break and then just also be reasonable about it. If you're wearing pants with a belt, they're going to shift throughout the day. They're going to move up and down a little bit, which will affect your break and life goes on. If you're wearing a very cropped leg silhouette or a very stacked leg silhouette, you should have a good reason to it. It should be part of aesthetic language.

Alison Stewart: Is there anything you see regularly that you just wish would go away?

Derek Guy: When my account started growing, I wanted to lean away to not make those pronouncements because I didn't want everyday people to feel bad about their choices, but there is something that I sometimes harp on, on social media, which is I think dress sneakers are really ugly. Dress sneakers is this phenomenon where people take the appearance of a dress shoe for the upper. They put a rubber sole on the bottom or like a sneaker sole. Not just a rubber sole, sneaker sole. To me, it looks like those T-shirts that have tuxedo prints on them like neither fish nor fowl.

Alison Stewart: [laughs]

Derek Guy: It doesn't work with a suit or sport coat and then it doesn't really work with casual wear. I think you're better off just buying a dress shoe and then buying sneakers like actual Nike, Adidas, Vans. Those are not only cooler, but they also work better with casual outfits.

Alison Stewart: Derek Guy has been my guest. He's the mastermind behind Die, Workwear! a.k.a., the menswear guy on X. Thank you so much for taking our listeners' calls. We really appreciate it.

Derek Guy: Thank you for having me on. This was a pleasure.

Alison Stewart: That is All Of It. All Of It is produced by Andrea Duncan-Mao, Kate Hinds, Jordan Lauf, Simon Close, L. Malik Anderson, and Luke Green. Megan Ryan is the head of Live Radio. Our engineers are Juliana Fonda, Jason Isaac, and Irene Trudel. Luscious Jackson does our music. Hey, if you missed any segments this week, catch up by listening to our podcast. If you like what you hear, leave us a great rating. I'm Alison Stewart. I appreciate you and I appreciate you listening. I will meet you back here next time.