Meet Derek Guy, Menswear King

Derek Guy has been writing about fashion for 15 years, but the Vancouver-born social media personality broke out in a big way following Elon Musk’s acquisition of Twitter. While most of the ensuing algorithmic tweaks have frustrated longtime users, exposure to the “Menswear Guy” has been a major positive.

Guy, now a San Francisco resident, can be found providing commentary on tailoring and personal style that makes building a fashionable, affordable wardrobe seem surprisingly easy to do, not to mention worth doing.

Guy’s encyclopedic knowledge of fashion’s trends and history is especially fascinating, but his timeline is more than just fun facts about pleated trousers and long, wide lapels. In an era of self-love, self-care and self-expression, he offers a guide to the outward reflection of one’s inner life. Fashion can be esoteric, and for many, its function unclear. Derek Guy makes it make sense.

Plus he dunks on trolls and right-wing politicians whose outfits often seem to inadvertently reflect their noxious hearts. In these instances, it’s not just education, it’s catharsis.

Needless to say, Guy has become an essential voice on the platform rebranded as X, where he now boasts 1.2 million followers. The founder of the fashion blog Put This On, Guy’s writing can be found in the New York Times, the Washington Post and Esquire, among others.

Recently, he spoke to the Tyee about Ken Sim’s fashion choices, dress as social language and the enduring popularity of Blundstones in Vancouver.

This interview has been edited for length and clarity.

The Tyee: I know you're very in-demand these days, sort of the go-to guy for men’s fashion. Which is weird since you’re never photographed. Is that to add mystique to your persona, or is it so you can still wear jorts in public?

Derek Guy: I’m just a fairly private person. There’s no real master plan behind it or anything.

Can I wear jorts in public?

Yes? Well, I'll be honest, I’m not a particular fan of jorts. But I am a fan of jeans and shorts. Not necessarily together, but if you’d like to wear jorts in public, I say, go for it.

Sometimes I get the sense that Vancouverites don’t really care much about fashion. One exception is our mayor, Ken Sim, who’s developed a reputation in some circles as kind of an unserious mayor. Part of this is the casual way he dresses. People seemed especially upset after he wore white sneakers at a Remembrance Day ceremony the other week. There is a debate over whether his style is disrespectful, given his position. Could you speak to that at all?

I think it’s always good to understand that people judge you based on your dress. If I was going to Remembrance Day, or a wedding or a funeral, I’d hold something in my heart. I’d wish to express in an external way my desire to honour people through my attire. The attire is only a reflection of what’s in my heart.

However, I don’t believe you should too harshly judge others for wearing something that you may consider inappropriate at the event. That person may not know better. That person may not have the money. That person may have rushed there.

I think it’s good to give some grace and understand that what you are truly looking for is to make sure that person also holds in their heart a desire to honour whatever, whoever they wish to.

That value, to me, is better expressed through other ways than attire. It can also be expressed through the way they treat people.

In Sim’s case, I think politicians have another layer that they have to consider, and that is that your dress choices sometimes take attention away from more important issues: your politics, your policies, your accomplishments.

I sometimes wonder if dressing down is a strategic choice for him. He’s a very rich man with very rich friends who wants to be seen, I think, as a man of the people.

That’s definitely been the case in U.S. politics since the 1970s. The suit has been dying a slow death since the end of the Second World War, and it started to go into sharp decline after the 1960s and ‘70s because of the civil rights movement, feminist movement, anti-war protests and the rise of different counterculture movements, and then, certainly, after Watergate made the suit seem too establishment.

Jimmy Carter, for example, when he went campaigning, he often took off his suit jacket, so he just campaigned in a dress shirt, tie and tailored trousers. Bill Clinton continued that tradition. Ronald Reagan sometimes campaigned in trucker jackets and cowboy boots and cowboy hats. Obama got rid of the tie. Ron DeSantis campaigned in a fishing shirt.

So whether a politician is rich or not, it’s true that politicians in general have tried to dress down to seem more relatable to the public. But it’s a delicate line. You might be venturing into territory where you end up looking inauthentic.

I’ll admit that all this attention on Ken Sim’s clothes feel a little disingenuous in a city where fashion tends to be secondary. What is your sense of Vancouver fashion?

I think of it as pretty similar to Seattle fashion, San Francisco fashion. It’s a very dressed down, practical, outdoorsy kind of clothing. Something for light rain. Sweaters. It’s just kind of generic middle-class clothing.

A lot of Vancouver’s clothing giants make outdoorsy athleisure. Lululemon, Arc’teryx, Herschel, Vessi. Do you have any opinion on how these brands have impacted men’s fashion?

I like outdoorsy clothing. I don’t particularly like the very modern version. There’s a company in Seattle named Crescent Down Works that does more heritage-y puffer jackets. I think that looks good.

We love a good puffer jacket up here.

If someone wanted to wear outdoorsy clothing, I would say, go back and look at the classic heritage styles of, like, the 1970s. A lot of those people wore puffer jackets and hiking gear, and I think they looked really stylish.

Any other tips on how to look fashionable in an extremely rainy climate? Everything is wet here.

It really depends on how the person wants to dress. Certainly, if they wanted to dress up, then you probably need, like, a trench coat or a Mac.

But most people are not looking to dress up. Most people want to do some type of casual wear. There are heritage-y kinds of puffer jackets from Rocky Mountain Featherbed. You can layer those over flannel shirts. Filson is obviously from the Pacific Northwest, and all of their clothes are essentially built for that weather. I think that stuff looks great.

I think you can wear Arc’teryx in a stylish way. There are a lot of more modern, techie kinds of menswear — techwear, which is a technical kind of look, and it involves brands like Arc’teryx, Acronym, Rosen X. Nike ACG is kind of in between street wear, tech wear and this kind of modern, outdoorsy clothing.

What would you recommend to trans masculine folks, or people who are otherwise unfamiliar with the rules, who are looking to enter the world of menswear? What’s a good place to start?

I don’t think that trans men have to approach building a wardrobe differently from cisgender men. I just got an email the other day where someone said, I’m a trans man. Do you have any tips on how I can dress for my body type? And I feel when I get that question, it’s similar to when I get questions from men who say I’m very short, or I’m very tall, or I’m very heavy.

Whoever you are, I don’t think that is the starting place. In fact, I think when you start from that, you often end up in a bad place, because whenever I read guides like that, they’re often like: How to dress if you're heavy. Oh, well, the solution is to not look heavy and then make yourself look more like this other idealized body type. I just don’t think that is the way to build a wardrobe.

So I would say, for trans men or for anybody, start first with thinking about dress as social language, and then think about how you want to dress. So if you’re a trans man, then I would think, do I want to take inspiration from, let’s say, Cary Grant and Gary Cooper, 1950s tailoring? Or do I take inspiration from the 1980s punk movement? Or do I want to dress like a 1970s hiker?

I recently did an interview with someone named CJ the X. I loved the video that they did.

Towards the middle of the video, they’re talking about their own struggles with dress and their inability to identify with, like, most aesthetics. And they were talking about how in high school, they put on a bit of makeup under their eye, and they thought, oh, this feels more like me.

And when they came home, their mom said, “Oh, you look like Adam Ant.”

Stand and deliver!

This person started to adopt all of these aesthetic markers of a world that reflected Adam Ant, David Bowie, some punk musicians. It all kind of came together.

I think you first have to think, what is the cultural language that I want to express? And then once you’ve identified that, then think, based on my budget and body type, how do I achieve that look?

What I’m hearing is that you have to find your language, and it can help to identify relevant style icons. I'm wondering if Vancouver has any style icons that you can think of.

I can’t think of any.

Maybe that’s why everyone around here, especially at this time of year, just wears Blundstones. I need something that's waterproof, but I feel like these are ugly boots.

I love Blundstones!

Rats.

What don’t you like about Blundstones?

Everyone wears them here. Vancouver is just gripped with Blundstone fever. But to me, it’s just kind of a flat look. Once you lose the laces, you know, it’s boring to me.

Like a black loaf of bread.

Yes. But I’m not the menswear guy. If you don’t want to wear Blundstones but you're a journalist for an independent outlet, say, so you’re definitely on a budget, what are your recommendations?

One that comes to mind is the LL Bean boot, which is even uglier than the Blundstone, but I think ugly in a charming way. Now, my impression is that Vancouver doesn’t get real heavy rain. It’s just like light rain.

It’s just constant. Not a lot of downpours. Just a lot of rain.

The other option that you can do, especially if you’re on a budget, is you can just waterproof your own boots. I would invest in a pair of good suede — not leather, but suede boots — and then I would spray them with a durable water repellent spray. You can just apply it at the beginning of the season. And then those are now your rain boots, because the water will bead right off.

There’s a company called Plasticana, and they do basically plastic rain shoes and boots. To me, that seems kind of overkill for what's essentially drizzly weather, but those are like $90, and I think they could look good in the same outfits that a pair of Blundstones would be worn.

There’s a company called Niwaki. It's an online Japanese gardening store, and they have heavy-duty, rubber-lined wellies that I think look really good.

I named both of them because, actually, Blundstones are not that cheap. They’re like $200. But two other ones to check out are Gardenheir, another online garden store, pretty stylish clothes, and they have a whole section on shoes that I think looks really good. The other one that I was going to recommend is MoonStar Alweather. They're a sneaker. They have a canvas upper and a rubber bottom.

They’re $250, so it’s a bit of money. But to me, they look cool.

I can’t wait to tell everyone that garden stores have the best wet weather boots. I’ll be the life of the party.