My Style Heroes: Elliot Duprey
Menswear isn't doomed!
Hi all! As evidenced by the
post slinging ire* (to the tune of calling it a ‘spindly glory hole’) that reverberated across the most prestigious corners of the fashion writing world, the so-called “menswear” sphere is going through a tenuous phase where it seems like everyone’s confused and distraught, caught, metaphorically, with their (front-pleated) pants around their ankles. Everyone, that is, except Elliot Duprey, whose fast-growing TikTok account is replete with incisive, determined perspectives on menswear, from the perfect proportions of a vintage safari jacket he found for $30 to the ethics of modern cashmere.*N.B. The author, at the very end of this piece, did give credit where due to Gen Z ;)
In a world of equivocation and watered-down sponcon, Elliot’s straightforward, knowledgeable approach to dressing might be startling—he will correct you if you misconstrue the image of the “Ralph Lauren Boy” [above], clown on the misguided attempts to artificially induce a seemingly AI-generated trend (in one such case, “eclectic grandpa”), and call out no less than Vogue on its apparent penchant for ripping off his prolific videos. In essence, though, his work is toward developing an accessible and delightful-to-watch entry point into menswear (again, used loosely—plenty of his archival wardrobe comes from the womens’ section, and he kills in pleated McQueen pants), free of the neologisms and in-jokes that make so many other menswear-oriented media outlets feel opaque or hokey, not to mention gender-exclusive.
Elliot’s good humor and sense of generosity were what left the biggest impressions on me when we talked a few weeks ago, and as a viewer, they’re what keep me coming back to his videos again and again, though if you held a gun to my head and asked me to define the difference between a Double Windsor and four-in-hand knot, I’d still be in dire straits. Luckily, I’ve never heard of a necktie-induced crime of passion, and even more luckily, Elliot’s generosity extended to HR—I hope you enjoy our talk below, touching upon everything from eBay misspellings to baby goat farms, and go follow Elliot everywhere for a clear-sighted perspective rarely seen in the fashion world, let alone menswear, in 2024.
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HR: You famously make TikToks about getting dressed (well) for your desk job—what's the best thing about not having fashion be your work?
ED: I work in management consulting in Chicago. It's just a regular nine-to-five, or like, eight to five. A regular desk job where I work in Excel and PowerPoint. I think eventually I actually want to make fashion my job, but right now, I really only know about fashion and I know that's a really hard industry to break into in terms of actually working in it. You need to have a large network, a lot of connections to get the job that you want to or work really, really hard for not a lot of money and probably be super broke in a city that you can't really afford for a while. I'm taking a safer option. I have an economics degree from a good school here in Chicago, and I was lucky enough to get a good job that pays me enough so I can take my free time and pursue my passion.
And afford clothes! What's your most specific saved search on eBay?
I really want a Ralph Lauren Polo coat. It's a very specific item. It has to be in size 38 R and it has to be either made in the USA or made in Italy. It's a 100% camel long coat and it has to be from a certain era, from the 80s or 90s. I search “Ralph Lauren Camel 38 R” in the men's coats category and usually nothing good comes up. I think once a year I’ll find something that is what I want and usually it'll cost more than I wanna pay...
I’ve found that searching common misspellings of words is such an important trick on eBay…
I found Chanel 1997 wool pants, but ‘pants’ was spelled PANYS, for like $27 dollars. It had the worst pictures ever, you couldn't even see anything, like half the pant was in the picture, but that was incredible. Unfortunately, they didn't fit me, so I ended up selling them a rare moment in which I did turn a decent profit. But you're so right that you have to account for people having no clue what they have on hand.
Once you've been searching for something for a while, you kind of get an eye for it, even when it's like a shitty, grainy photo and it looks like crap, you can tell when something is worth it, and oh my God, the rush. It's amazing.
It really is a rush. There's so many times it's happened to me with Tom Ford’s Gucci or McQueen—they'll be completely mislabeled, and oh yeah, I'll pounce.
What got you into fashion in the first place?
It's probably gonna sound lame, but I was a bit of a hypebeast in high school. That was like the easiest way to get into it. I made a decent amount of money flipping Supreme and stuff. I hope most people look at me and think like I have an actual, serious sense of style now, but yeah, that was it. I started caring about what other people thought of what I was wearing, that's how it started. That really helped me find myself in a lot of ways, and through that I was able to develop a lot of personal self-confidence, be happy with who I was. It was a big, big evolution from senior year of high school till senior year of college. I went from wearing Supreme box logo hoodies to wearing archival Alexander McQueen [below].
I really admire people like you who are very opinionated and know what they're talking about when it comes to fashion.
I think that's a hard line though. I am definitely opinionated and I think my friends would say my real life persona is a lot more divisive than my online persona. I don't want to say that I'm probably a little bit meaner in real life than I am online, but you want people to like you online, right? I don't want to attract hatred and I don't want negativity spreading from my content. Clothing is not supposed to be negative. It's not supposed to be a judgmental sphere, so however much I may internally hate on someone, I would never bully someone, but… there are still some cool Supreme pieces, I would say, but I might think “You're still wearing that kind of garbage?” for most of the hype-ier stuff.
What's a cool Supreme piece? I haven't seen any, but I also haven't sought out Supreme, so I would love to know what is cool there.
Supreme did a collaboration with Undercover [above] back in 2016 or something [ed. note: someone please buy this Lupin t-shirt so I don’t add to my ridiculous collection of anime tees] that I thought was decently cool back then. They've had some interesting collaborations. Off the top of my head, I can't really tell you what they were, but it was cool when not everyone was wearing it, and then it became super uncool because everyone was wearing it, and now because it’s less cool, the people who really know what was good stand out. I think there's a level of taste within that.
What's the biggest menswear styling mistake you see people making?
Oh, goodness, where do I start? A lot of people don't know their own size. I think that's something that's very important, something that I see all the time. Blazers are one thing that used to be super important, right? Blazers and suit tailoring, all the way up until the 90s, people would focus on that, men would usually wear them every day to work, and now most men have on the most ill-fitting blazer or jacket or whatever. It might not even be their fault—everything's off the rack and made of polyester and garbage. Knowing your size and how to find something that is actually flattering on your body is really difficult. I think a lot of “regular guys” going to the office don't really know their sizing. The sizing itself is not that hard to figure out, you just have to take your measurements…
To be fair, I don't usually shop in strictly menswear departments, but in womenswear, the sizing is actually insane. It makes zero sense and has no consistency.
I own plenty of women's clothes and they range from, like, size four to size 16. I'm totally with you. The fact that they could be from the same brand is even worse. But that's why measurements are so key, and that's why if you're going to shop online, the first thing that you need to know is your measurements, because if you're not using measurements, you could think that you know your size in a brand’s clothes, so this one item that you're trying to buy was actually made two years earlier and its sizing then was completely different for this item. It’s frustrating.
There are so many menswear mistakes. I'm really into tailoring and more traditional, older-school menswear, and I think there's a lot of mistakes that people make in that sphere. Suits that aren't full, suits that don't fit, lapels that are too slim—their buttoning point is too high. People wearing a suit jacket separate from the suit pants thinking it's a blazer. It's not a blazer, that's a suit jacket. It doesn't go with jeans. Sleeve lengths not working. I can go on and on and on… that stuff bothers me a lot.
Are you on Twitter?
…………. That was too long of a pause. I mean, yeah, but I'm just on a really nerdy corner of Twitter.
That's fine! There's this one menswear account...
Derek (@dieworkwear)!
Yeah, Derek, exactly! I've learned so much from him. Before I found his Twitter, I would wear suits and other stuff like that, but I couldn't see something and understand it. I’d be like, this looks good or this looks like a classic, but I didn't understand exactly why. I think it was more of an eye for aesthetics rather than an actual understanding of the garment and the history of the suit. Then I read some of his stuff, it was incredible—I've learned a lot from his material and through that, I've started reading more of the reference material. Now with every single guy I pass in the street of Chicago, I'm like, why the heck is he wearing a Double Windsor [knot below] with a button down? He looks like an absolute fool.
I don’t even know what you’re talking about but I’ve probably somehow worn a Double Windsor with a button down at some point in my life…
The fun thing about menswear is that the rules are made to be broken, but they're only made to be broken if you know what the rules are to begin with. If you're doing something intentional and there's meaning behind that switch, then you're doing something interesting, but if there's no intention, it just looks like you have no education in menswear.
There has to be a baseline for there to be a subversion?
Absolutely.
Do you have any menswear icons?
So many, oh gosh. I just did a video on Paul Newman [above], I think he had some of the greatest style:
Steve McQueen, horrible person, but had a really cool style as well:
These guys are general pinnacles of style. I love Miles Davis, he had some freaking sick style. There's this one photo of him playing the trumpet with bell sleeves that are made of an, almost pleated, sweater or cotton. It looks so cool:
Richard Biedul on Instagram—I think he has exceptional style. He's like a model, but everything that he models and the stuff that he wears personally is really, really cool:
Stefano Pilati used to be the creative director for Yves Saint Laurent, I believe, but he has incredible personal style himself:
Do you have any other interests that intersect with fashion? I personally am a huge anime fan and am obsessed with Wisdom Kaye, who does the wild anime-inspired outfits…
He’s ridiculously good. His style is so cool. His wardrobe is also probably worth upwards of one to two million dollars. He actually just followed me back, like a month ago. I was in the office and I screeched. It was really bad, actually. Then he commented on one of my posts, something like “This coat is on my Grailed wish list.” I was like, if Wisdom likes my coat, it's a good fucking coat.
I think I just have a general interest in aesthetics—I want everything to look nice like be nice when I'm there. My entire apartment is filled with secondhand mid century modern-or-adjacent furniture from Facebook marketplace or vintage stores around Chicago. But that makes a ton of sense, furniture and interior interior design go hand in hand with fashion. I talked to one of my friends about this recently—people who have an interest in one but have a complete disinterest in other aspects of aesthetics… if you're super into fashion, but you sleep on a mattress on the floor and have a folding table and a flip chair or whatever, are you really into fashion? There's a certain level of aesthetics that are really important in expressing yourself and being interested in these things. Does that make sense?
Yeah, but if you spend all your money on Lumps and Bumps, all you can afford is a mattress on the floor, so...
That is also super, super true.
Do you have any favorite visual artists?
I really like Robert Motherwell, a Dada artist. I like Roy Lichtenstein, that's pretty basic, but Pop Art is really great. I have a photo of calla lilies that my dad took that's always behind me in my TikToks, and everyone's like, is that a Robert Mapplethorpe? I’m like no, it is not, but I do really like his stuff.
What are your favorite all gender/gender fluid/genderfucking labels?
Vintage McQueen. He knew how to tailor for anyone, and he knew how to do it very, very well. That’s a reason I collect it. I actually probably own more womenswear from vintage McQueen… not probably, 100%. I own more womenswear from him, 'cause it's easier to find. HOPE Stockholm is a brand that I own one jacket from, but every single piece that they have is truly unisex. I really like it—it's my casual going-out jacket if it's not super cold out.
Most of the vintage stuff I wear is pretty “men's”-focused. I think vintage Armani can be very gender neutral—it can cover everything in a lot of ways. I think for a lot of people, that can be a very comfortable way of dressing. Someone nonbinary stitched one of my original Armani TikToks saying that they were super inspired and bought some vintage Armani stuff, and that it made them feel a lot better to be wearing these slightly masculine-leaning but also just wear-over-everything kind of vibes. Of course, Comme des Garçons makes things for anyone. That's super expensive though.
The first label I think of when I think of genderfucking is Dion Lee—so cool.
Jacob Elordi wore a Dion Lee corset and that actually, like, broke so many people. He looked really good in that.
I was also going to say Lemaire. I really like Christophe. I am on the hunt for multiple things from Lemaire, that's like part of my eBay searches. I like everything Lemaire, but it's women's and men's coats that I'm always looking for—they design them pretty evenly.
It's very similar to vintage Armani in the sense that you can kind of cloak yourself in it and it's made of wonderful materials, wonderful for layering, everything flows and looks so cool. I think The Row and Lemaire are often grouped together, but in my opinion Lemaire is a lot better at styling and cutting. I do like The Row and I think it uses really good materials—I have put on one The Row cashmere sweater and it really did feel like a cloud.
I'm sure, but there is just nothing on God's green earth that justifies that kind of markup. I know how clothes are made, I know what prices look like, and it’s just impossible for something to be that expensive.
Yeah. Even Loro Piana is not charging $3,000 for a cashmere sweater, and they have their own dang baby goat farm, so.
I am really passionate about accessibility in fashion, Like physical accessibility, gender accessibility, but then also financial accessibility. That's why I really like people like you who wear vintage a lot, because that's more accessible, it makes more sense for a lot of people…
Accessibility and fashion are two things that feel so separate a lot of the time. That was one of the original reasons I started my TikTok—people were constantly asking me, like, “You have really good clothes but like you found them for, theoretically, really good deals?” Proving to people, showing people the prices you've paid for every single item opens up the dialogue of high fashion for people who maybe never considered it—not like not that high fashion is the pinnacle of fashion, but it's…how do I put this?
It can be easier to develop taste when you already know that something is considered tasteful by others. I know now that I can go to a vintage store and I don't need to see a label. I don't need anything.I know what I like, but I think I developed that by owning, going through, and buying and selling a lot of designer pieces. That gives you a baseline of what can be good and what people have considered good in clothing.
I hate Coco Chanel because she was a Nazi, of course, but she had that whole thing where it was like “Take off one thing before you go out” or whatever [which I kind of hate too]. Do you have any clothing rules, mantras, or die hard beliefs that you proselytize to people, or anything that you keep in mind when you get dressed?
No, I don't have any rules. Well, I only tie a four-in-hand knot, that’s actually the only thing. I have a video about it that I made a few weeks ago, but it's a super basic tie knot. It's a schoolboy tie knot in England, but it's very Ivy. It's slim, it's small, which works for me, 'cause I'm a tall, skinny guy, but I also just like it. It's a little bit asymmetrical, which is weird because I'm a very symmetrical, detail oriented, everything needs to be in its place person, so it adds a little bit of a quirk:
Other than that, I think the biggest thing I would tell my friends when I shop with them is that I'm super picky about the material composition of something, no matter what brand it is, no matter anything. Wear natural fibers as much as you can and don't buy things with stretch if you can, because eventually, that stretch is going to go. Wash your jeans once every 50 wears or less—that's something else I'll tell my friends.
Ok, I probably do have rules, but I don't think of them when I get dressed every day. I don't care about mixing black and navy or stupid stuff like that. They look good together. Actually, technically, you’re supposed to wear black shoes with a navy suit.
The more you know! Thank you SO much for your time and knowledge, Elliot.
Any time!
Thank you again, Elliot, for such a generative talk—you inspire me not to settle for accepting tropes or trends for what they are, but to investigate their histories, imagine their implications, and question their value to my personal style. I can’t wait until Vogue sheepishly shows up at your doorstep with a bouquet of flowers like an unfaithful husband in a rom-com.
And thank you, readers, for being here—as always, I am thrilled you are!
<3 HR
I love this interview and Elliot’s style! Definitely an inspiring take on menswear. Also the tip on misspelling for online thrifting is gold!