The Twitter Menswear Guy Takes Calls

Summary

Podcast Episode Summary: "The Twitter Menswear Guy Takes Calls"

Podcast Information:

• Title: All Of It
• Host: Alison Stewart
• Description: ALL OF IT is a show about culture and its consumers, aiming to engage thinkers, doers, makers, and creators about the what and why of their work. The show builds a community around diverse perspectives, reflecting the vibrant culture of New York City.

Episode Details:

• Episode Title: The Twitter Menswear Guy Takes Calls
• Release Date: January 17, 2025
• Host: Alison Stewart
• Guest: Derek Guy, known as the "menswear guy," with over a million followers on Twitter for his comprehensive threads on men's fashion history.

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1. Introduction to Derek Guy

[00:37] Alison Stewart: Welcomes Derek Guy, the "menswear guy" known for his detailed and informative threads on Twitter about men's fashion history. Derek has cultivated a substantial online following by addressing questions ranging from suit brands to jacket fit and the distinctions between suits and sports coats.

[01:08] Alison Stewart: Encourages listeners to call in with their menswear questions, setting the stage for an interactive and informative session.

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2. Derek Guy’s Journey into Menswear

[01:46] Derek Guy: Shares his early interest in fashion, which was initially sparked not by clothing itself but by its role as a "subcultural uniform." He was deeply involved in the music and dance club scenes, where fashion served as a key identifier within various subcultures.

[02:25] Derek Guy: Discusses his personal heroes and influences in men's fashion, particularly those from the freestyle dance scene who wore brands like Polo Ralph Lauren. He delves into the origins of classic menswear staples like tweed jackets and chambray shirts, highlighting his journey of discovering the historical roots of these garments through menswear blogs and forums in the early 2000s.

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3. Growth and Shift in Content Strategy

[03:29] Derek Guy: Explains a pivotal moment at the end of 2022 when his Twitter account surged from 50,000 to 100,000 followers. This spike was triggered by a viral thread critiquing Dave Portnoy’s Brick Watch and an ensuing discussion about the cashmere industry. Realizing that his audience preferred informative content over niche jokes, Derek shifted his focus to more substantial threads, resulting in continued growth and broader recognition, including features from major publications like the Washington Post.

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4. Listener Q&A Sessions

A. Shopping on eBay and Thrift Tips

[05:15] Reid from Brooklyn: Asks for recommendations on shopping for vintage menswear on eBay, specifically sweaters and pants.

[05:56] Derek Guy: Provides detailed advice on finding quality sweaters, emphasizing that country of origin is no longer a definitive indicator of quality. He suggests searching for specific fibers like cashmere or Shetland wool and filtering results by regions known for quality knitwear, such as Scotland. Derek also advises checking measurements meticulously to ensure proper fit when purchasing online.

“An easy way to find a good sweater is to search for the fiber you’re looking for, like cashmere or lambswool, and then include the country of origin, such as Scotland, to filter high-quality options.” [06:16]

B. Surgeon Cuffs on Suits

[08:36] Listener via Instagram: Inquires about the discontinuation of surgeon cuffs on blazers and suits, wondering why designers have moved away from them.

[08:48] Derek Guy: Argues that surgeon cuffs haven't disappeared but are often misapplied in ready-to-wear suits to signify quality. He explains the historical purpose of surgeon cuffs and critiques their use in modern ready-made garments, advocating instead for unfinished cuffs that allow for alterations without compromising the garment's functionality.

“Designers actually started using surgeon cuffs because consumers associate them with quality, but for ready-to-wear suits, unfinished cuffs are preferable as they allow for adjustments.” [08:48]

C. Menswear as a Language

[10:23] Alison Stewart: Highlights a listener's testimonial about relying on Derek's advice for wedding suit shopping and poses a question about high-end pre-owned suits versus less expensive off-the-rack options.

[10:34] Derek Guy: Compares menswear to a cultural language, emphasizing that dressing is a form of self-expression and group identification rather than merely following trends. He suggests adopting an aesthetic inspired by cultural sublanguages to create coherent and personal style statements.

“Clothing is a form of social language, a way to identify with a group and express yourself as an individual within that group.” [10:34]

D. Buying Pre-Owned Suits

[12:23] Derek Guy: Advises that pre-owned suits can be a viable option, especially when purchased in person, to ensure proper fit and quality. He recommends seeking out donations from affluent neighborhoods or charity shops associated with high-quality organizations for better selections. For online purchases, he stresses the importance of verifying measurements and ensuring easy returns.

“It is better to shop in person at a secondhand store to ensure the suit fits well, especially since suits are less forgiving than other garments.” [12:23]

E. Styling Jeans with Shoes

[14:56] Reed from Forest Hills: Asks for advice on pairing jeans with shoes and selecting appropriate cuts and styles for everyday casual wear.

[15:10] Derek Guy: Recommends a slimish straight leg cut, such as Levi's 501 Vintage Fit or similar styles from brands like Gustin. For shirts, he suggests opting for casual button-ups like plaid flannels or textured oxford shirts to complement the jeans. Regarding footwear, he advises choosing versatile options like Chukka boots, sneakers, or penny loafers, avoiding overly dressy shoes like Oxfords for casual outfits.

“Think of your ensemble as a cohesive unit where formality and style harmonize; this approach simplifies decisions about fit, color, and footwear.” [15:10]

F. Suit Vest Button Rules

[15:56] Mike from Bed Stuy: Inquires about the etiquette of leaving the bottom button of a suit vest unbuttoned.

[15:42] Derek Guy: Confirms that traditionally, the bottom button of a vest should remain unfastened. He explains the historical origin of this rule and notes that while some modern vest cuts may not allow buttoning the last button without affecting the jacket's fit, the general guideline remains to leave it open to maintain a polished appearance.

“Generally speaking, the bottom most buttons should not be fastened, adhering to the classic rule to maintain the vest’s proportion and functionality.” [15:42]

G. Suits for Larger Frames

[19:42] Mike: Seeks advice for taller and larger individuals (6’7”) on selecting suits without relying solely on custom tailoring.

[20:13] Derek Guy: Acknowledges the challenges faced by larger individuals in finding well-fitting suits due to the decline of the tailoring industry. He suggests seeking out specialized stores like O'Connell’s in Buffalo, New York, which offer larger sizes and custom paper patterns. Derek emphasizes the importance of focusing on fit specifics, such as shoulder alignment and jacket length, and recommends shopping in person when possible to ensure garments accommodate unique body dimensions.

“The most important thing is the fit of the shoulders and ensuring you can move comfortably without the suit feeling restrictive or ill-fitting.” [20:13]

H. Color Coordination: Black with Blue

[22:35] Derek Guy: Discusses the appropriateness of pairing black with blue, asserting that it depends heavily on context. He distinguishes between formal combinations, like black ties with navy suits, and less traditional pairings, such as navy shoes with black suits, which he considers unconventional and stylistically inconsistent.

“A black silk tie looks fantastic with a navy suit, but navy shoes with a black suit don’t align with traditional styling norms.” [22:35]

I. Suit Pants and Ankle Length

[23:34] Listener Inquiry: Requests advice on the ideal length of suit pants—whether they should cover the shoe or show the ankle.

[23:51] Derek Guy: Advises adhering to classic guidelines: trousers should either have a slight break where the hem touches the top of the shoe or have one subtle break. He emphasizes consistency with the shoes worn during hemming and suggests that any deviations, like cropped or stacked pants, should align with a deliberate aesthetic choice rather than casual experimentation.

“The pant should either have a shivering break or one break, maintaining a straight line from hips to shoes for a classic and versatile look.” [23:51]

J. Fashion Pet Peeves

[25:14] Derek Guy: Expresses his disdain for "dress sneakers," which he considers aesthetically compromised. He explains that these hybrid shoes fail to fit seamlessly with either formal or casual outfits, recommending instead the use of distinct dress shoes and casual sneakers to maintain clarity and cohesiveness in one’s wardrobe.

“Dress sneakers look like a midway point between dress shoes and casual sneakers, failing to work well with either formal or casual ensembles.” [25:14]

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5. Conclusion

[26:04] Alison Stewart: Wraps up the interview by thanking Derek Guy for his insights and contributions as the "menswear guy" behind Dye Workwear and his influential presence on social media.

[26:16] Derek Guy: Thanks Alison Stewart for the opportunity to share his expertise.

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Notable Highlights and Insights

• Cultural Language of Fashion: Derek emphasizes that fashion serves as a form of social language, enabling both individual expression and group identification.

• Evolving Menswear Trends: He highlights the shift from niche, humor-based content to more informative and educational threads that resonate with a broader audience.

• Practical Fashion Advice: From sourcing quality garments online to understanding the nuanced rules of suit styling, Derek provides actionable tips for listeners to enhance their personal style.

• Industry Challenges: Addresses the declining availability of custom tailoring and offers solutions for individuals with unique sizing requirements.

• Aesthetic Consistency: Stresses the importance of maintaining coherence in outfit formality and style to achieve a polished and intentional look.

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Quotes with Timestamps

1. “An easy way to find a good sweater is to search for the fiber you’re looking for, like cashmere or lambswool, and then include the country of origin, such as Scotland, to filter high-quality options.” [06:16]

2. “Clothing is a form of social language, a way to identify with a group and express yourself as an individual within that group.” [10:34]

3. “Generally speaking, the bottom most buttons should not be fastened, adhering to the classic rule to maintain the vest’s proportion and functionality.” [15:42]

4. “A black silk tie looks fantastic with a navy suit, but navy shoes with a black suit don’t align with traditional styling norms.” [22:35]

5. “Dress sneakers look like a midway point between dress shoes and casual sneakers, failing to work well with either formal or casual ensembles.” [25:14]

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Final Thoughts: In this episode of All Of It, Derek Guy offers a wealth of knowledge on men's fashion, blending historical context with practical advice. His ability to demystify complex fashion concepts and address listener inquiries underscores his role as a trusted authority in the menswear community. Whether discussing the origins of classic garments or navigating the challenges of finding well-fitting suits, Derek provides valuable insights that empower listeners to cultivate their personal style with confidence and understanding.

Transcript

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[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. And 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. 2124-3396-9221-2433. WNYC. It's your chance. The menswear guy. Your question or you can send us a message at olivenyc. So 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. I didn't have my interest wasn't specifically in clothes, but clothes was part of a kind of subcultural uniform. I was really into music at the time and went to dance clubs. And I think if you're part of any scene, you get a sense that there is a kind of uniform for that scene. And 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 through music to men's fashion?

[Derek Guy]

Well, I don't know if they were all kind of dancers in this burgeoning underground scene called freestyle dance. And a lot of those guys were dressed head to toe in polo. And I thought they were just the most stylish dudes in the scene. So through them I got introduced to Ralph Lauren. And when I went to Ralph Lauren flagships, that's where I got introduced to tweed jackets and chambray shirts and oxford button downs. And 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 Savar. And just, I just kind of 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 kind of 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]

That happened at the end of 2022. From 2011 to October of 2022, I was mainly making jokes for fellow menswear nerds. So there were a lot of jokes about like, niche Japanese workwear brands and, you know, buying too many olive colored jackets and things like that. But the end of 2022, Dave Portnoy released. He started a watch brand called Brick Watch. And I criticized, I said I thought it was a. It was not a very well made watch and it wasn't worth the price that he was asking. And one of his followers went into my thread and said, well, how's this different from Ra Thorne buying a $50 cashmere sweater and selling it for 500? So 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. And that thread went viral. After that, I got phone calls from like Washington Post journalists and people asking me for quotes for articles on how to find good cashmere sweaters. And I realized that 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. And once it ballooned to that size, I felt like I couldn't make any more jokes about niche Japanese workwear brands because it wouldn't land and it wouldn't make any sense. So I continued to do, like, more informative threads instead of these snarky in group jokes. And people seem to like that. And yeah, 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, Reed. Thanks for Calling all of it. You're on with Derek.

[Reid]

Hi, Alison. Long time, long time. And Derek, big, also a long time fan. And so I've kind of 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. Pure Cardin is great for that. I'm probably blowing up my own spot doing that vintage L.L. bean. I was wondering if you had any other recommendations for shopping on ebay. And 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 to 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, so I can't explain any of the reaction I research. I mean, I just, 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 like Shetland wool and stuff. And so that's been very helpful. Yeah, a lot of sweaters, I really. With pants, it's so hard because the fit is just gonna be something that you have to try. But yeah, definitely sweaters, vintage shirts, any tips you have for those are much appreciated.

[Derek Guy]

So for sweaters, a really easy way to find a good sweater is. I don't think it's, 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, 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. But now people are making high end sweaters. But it is true that in the 19, prior to, I would say the 1990s, 1980s, most of the good knitwear was coming from Scotland, for example. So a very easy way to find a good sweater is on ebay. You'd search for the fiber that you're looking for. So you'd search for cashmere or lambswool or Shetland wool, merino maybe. And you do, in parentheses, Scotland, comma, Scottish, do a search and then click There's a checkbox for title and descriptions and then click search again and that will pull up all the listings for that sweater in that was made in Scotland or that was made in Scotland. And the reality is that in Scotland, many of those companies were chugging along with really good machinery, really skilled workforce, and they simply did not update themselves very well. So in Italy, for example, a lot of Italian production ran on being very fashionable, which sometimes just didn't age very well. And 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. So 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, you know, pit to pit measurement, length measurement, 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. And 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. So let's explain what a surgeon cuff is. Surgeon cuff is on a suit jacket or sport coat. The buttonholes will be cut so that you can unbutton, you know, the buttons. And historically that was done on custom suits. So that supposedly, I mean, you know, who really knows, but supposedly like a surgeon could roll up his sleeve to wash his hands without ruining his, his suit jacket. The thing is, is that over time people have started to associate that with quality and 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. And 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. So yeah, 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. You know, like a celebrity wore something, so now I have to wear something. Or the trend is slim fit, or the trend is, you know, very baggy fit. So I have to conform to this. Or they think of it in these pseudo scientific terms like, oh, does black go with blue? Or you know, I am this body shape and how do I dress for this body shape? I don't think of dress in that sense. Address in terms of cultural language and going back to your first question, when, you know, when I was into a certain music scene and going to dance clubs, there was a certain kind of look for that group. And 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. And I think if you think of style in those terms and think what are the kind of cultural languages that I want to emulate that I think are good and fit my personality identity, it's much easier to answer those questions of how should something fit and what colors go with what. And I also think that's how we interact with clothing. Clothing is a form, a way for us to identify ourselves with a group but also express ourselves as individuals within that group. So 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. And then the other text says, hey Derek, any thoughts on high end pre owned suits versus less expensive off the rack new? So 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. I mean, 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. But a suit is cut in such a way that it's much less forgiving. So 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. So I encourage people to if you're shopping secondhand, it is better if you can shop in in person at a secondhand store. And an easy way to find better suits or better made suits, frankly, is to find out where rich people donate clothes in your area. So often those will be located in wealthy neighborhoods or sometimes they might be at charity shops that you know are benefiting some organization that rich people, you know, care about, like the, you know, the ballet company or the orchestra or whatever. Sometimes churches in rich neighborhoods will have, you know, really nice donations. If you have to shop on ebay, then obviously check those measurements and make sure you can return easily. It is, I would not, I would never get too hung up on brand names, especially since the market has so many diffusion lines. But generally speaking, if you see a garment made in America or England, historically, it will be of a higher quality, although again, that's, I don't think it's true anymore.

[Alison Stewart]

I'm talking to Derek Guy, the mastermind behind dye workwear, AKA the menswear guy. We are taking your calls. Do you have a men's fashion or other style question? Give us a call, 212433, WNYC, 212433. 9692 will have more, including a question about suit vests after the break. You are listening to all of it on wnyc. I'm Alison Stewart. My guest is Derek Guy, the mastermind behind dye workwear. He's the menswear guy. We're talking fashion. Let's talk to Mike. Hi, Mike.

[Reid]

Good afternoon.

[Derek Guy]

How are you doing?

[Alison Stewart]

Well, what's your question.

[Reid]

On suits? When you have a suit vest, the very bottom button I was always told should remain open. Is that a part best rule or what is the rule around suit vest?

[Derek Guy]

Yeah, I mean generally speaking, the bottom most buttons 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 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. So on certain vests you can button the last button. But generally speaking, you're 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. And it was just because during in 2011 there was this like heritage craze for workwear and everyone in the city is dressed like a lumberjack. I actually love and wear workwear, but I was just, I literally typed something into Tumblr, which was a Tumblr blog at the time. And it was a friendly jab at a friend of mine who really loves workwear. And I didn't think that the blog would grow. And 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. So 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?

[Reid]

Yes, so I'm a 50 year old male and I was wondering what style.

[Derek Guy]

Advice would you give in terms of wearing jeans with shoes? How does he feel about that? And also what cut and style would work best in terms of, you know, everyday casual wear? My feeling on any question on how to dress is always contextualized by what is the aesthetic that you're inspired by. But generally speaking, people who are asking, you know, like, if you're inspired by like hip hop, then obviously you're, you know, if you're inspired by like 90s hip hop, then you're wearing really baggy jeans. If you're inspired by 70s punk, you're wearing very skinny jeans. But most often if someone's asking this question, they're just kind of getting their first steps into dressing better. So in that regard, I think a really easy cut is to wear.

[Reid]

A.

[Derek Guy]

Cut that's not overly slim, but it's a slimish 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 are popular at the moment. And it's comfortable through the leg but not baggy. And 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. It's like, I want to say those are like maybe like 250 or $300, which is a big ask. So 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. So instead of like your dressy white poplin spread collar shirts, consider plaid flannel shirts or chamois shirts or like a light blue oxford cloth button down. Anything with some texture or pattern is going to look a little bit less dressy than those stark pinpoint white poplin shirts that, you know, people wear to the office. And in that sense, you're kind of combining a slightly more casual item with another casual item, which is your jeans. And then obviously for your shoes, I would again go for something, you know, that can be anywhere from Chukka boots to sneakers to penny loafers. You know, anything I would say, except for oxfords. Oxfords are the kind of lace up close facing shoe that you'd 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 like the really easy one, you know, one sentence kind of 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.

[Mike]

Yeah, thank you so much. Love the show. Derek. I'm a bigger guy. I'm about 6 foot 7 and I just got my first suit a couple years ago, custom made, but I don't know a lot about suits and I invested a lot in it. And it's really the only suit I have. For bigger people who need, you know, special sizing. What advice would you have for them when looking for a suit if, especially if they don't have, you know, 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. You know, the US used to have thousands of tailors, used to be a tailor in every town, and that is no longer the case. And the suits that you find are often, you know, fit a very narrower scope of people and they come in a very limited number of fabrics because the store has to figure out how to make money to pay rent. So 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 and they will often draft a new paper pattern as they scale up into larger sizes. I have seen some people look pretty good. I mean, I know they have like a very bad reputation, but I've seen some people look really good in like Jose 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, ends about halfway from the back of your collar, 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. And then obviously make sure that you can button the jacket without straining and importantly, hug somebody. Like, you can move comfortably without feeling like the vaccine is going to rip those. You know, it's going to be hard if you're 67 and you're a larger guy. That is generally, you know, if you want a really good fit, that's generally the world of custom. And we are unfortunately in a world where there just aren't very many good custom tailors. And custom tailoring is expensive. I feel for people who I can't give a better answer to, but that's my answer.

[Alison Stewart]

But it's great. You know what, I was on your, on your feed and you point out that Matty Matheson from the Bear has great style.

[Derek Guy]

Yeah, I think he is 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. But among celebrities and also among non celebrities, I think he's one of the best. I suspect his suits are custom tailored though. Yeah, he probably gets custom tailored.

[Alison Stewart]

The question is, does black go with blue?

[Derek Guy]

Totally depends on the context. You know, a black silk knit tie or a black grenadine tie looks fantastic with a navy suit. A navy suit is. Or black oxfords are really natural accompaniment to navy suits because of the history of, you know, how London men used to dress for business and that's where we get most of our suit rules. Does a black polo go with black or does a navy polo go with black jeans? Not really, because there's no like social history around that. It's just a, you know, it's not, it's not terrible, but it's like, it's like Whatever. You know, would, for example, with navy shoes, go with a black suit? No, because that's a. 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 we have.

[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. And we have very different views about this.

[Derek Guy]

Very, very dependent on the outfit that you're creating. You know, there are certain kind of outfits where it's fine to wear a slightly more cropped leg, and there are certain outfits where it's actually fine to have a stacked leg, like, you know, to have really long pants. But generally speaking, if someone's asking this question, they're asking about very basic outfits. And in that sense, I kind of think that you should stick to a very classic rule, which is the pant 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 leg, 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 this 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, you know, life goes on. But if you're. If you're wearing a very cropped leg silhouette or a very stacked leg silhouette, you. You should have, like, a good reason to that. It should be part of, like, a aesthetic language.

[Alison Stewart]

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

[Derek Guy]

You know, when my cancer growing, I wanted to lean away to not make those kind of pronouncements because I didn't want, like, everyday people to feel bad about their choices. But there. There is something that sometimes harp on on social media, which is I think dress sneakers are really ugly. And dress sneakers is this phenomenon where people take the appearance of a dress shoe for the upper and they put a rubber sole on the bottom and or like a sneaker sole, not just a rubber sole, sneaker sole. And to me it looks like those T shirts that have tuxedo prints on them like neither fish nor foul. 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 dye workwear, AKA 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]

And that is all of it. All of it is produced by Andrea Duncan Mao, Kate Hines, Jordan Loft, Simon Close, Elle Malik Anderson and Luke Green. Megan Ryan is the head of Live Radio. Our engineers are Juliana Fonda, Jason Isaac and Irene Trudell. 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 and I will meet you back here next time.

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