If you spend any time on Twitter, you probably know the handle @dieworkwear by heart. It belongs to Derek Guy, aka “the menswear guy” expert extraordinaire.
I have to confess that until I started writing this essay, I wasn’t even sure if Derek Guy was his real name. I hadn’t bothered to check because I trust him implicitly. Perhaps controversially, I enjoy nearly all his posts, so why wouldn’t I trust him?
He blends sartorial insights with pop cultural awareness, self-deprecation, and sarcasm. He covers topics like men’s suits (a staple), the now infamous “collar gap,” the “level of tailoring that’s very rare to see nowadays even on the wealthy,” his disdain for dress sneakers, young Harrison Ford in short shorts, and ample praise of the Polo Ralph Lauren bear — all part of a larger than life online persona.
Derek Guy has become a widely acquired taste, with Elon’s For-You-ificiation of Twitter playing a big role. Pre-Fall 2022, Guy had just tens of thousands of followers. His account growth since is fascinating: in July 2023 he got over 100K followers; in April 2024, he got 180K+ followers. He now has over 900K followers.
I’ve also found it fascinating to ponder what has made Derek Guy so successful.
My curiosity stems in part from my curiosity about the ingredients for success in public arenas, in part from my being a closet fashion appreciator (in my mind a bit of a connoisseur), and in part from my belief that there are universal lessons to be learned from studying such a character.
I’ve identified some standout attributes — 13, to be exact. This isn’t some comprehensive guide to achieving meteoric success, but I think there’s something in it for everyone who wants to share any of their thoughts with the world:
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Become an expert in one thing that’s more specific than feels comfortable.
Find a way to be an authority on something you genuinely enjoy thinking about. Start with a broad subject (e.g. fashion, tech, sports) and then niche down, like way down. If you’re still too far from being an expert, become an expert in the experience of trying to become an expert. This might feel uncomfortably specific and limiting at first, but that’s the point.
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Be obsessed with the craft of that one thing.
Perhaps the most notable thing about Derek Guy’s posts is his obsessive attention to creation and quality at a micro level. This is caring about the craft — not just caring about the end result but also every input along the way. And being obsessed with the craft of anything is the exact opposite of superficial.
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Only talk about that one thing and things that relate to it (at first).
If one of your main goals is to grow your audience on a given platform, it’s crucial to stick to your area of expertise and related topics. This allows people to associate you with the topic they’re interested in before they connect with you on a personal level. I’d say an 80/20, maybe even 90/10 split is a good start, where the majority of your content is on your core topic. Once your audience is sufficiently engaged with your work, you can ease them into accepting and maybe even caring about your other interests and personas.
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Teach people something, whether they want to learn or not.
Educate your audience even if they aren’t actively seeking the knowledge. I’d say make at least two-thirds of your posts educational (others can be more conversational or humorous for example). You didn’t ask the internet what a collar gap was, but you found out anyway. Force people to learn by default.
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Find a way to make the thing relevant to more people than it would seem.
Why should everyone care about men’s suits? Maybe because the principles of what makes a suit look good are many of the same principles that make anything look good on anyone. It’s obvious why people would care if that’s true. Your job is to bridge the divide between niche and universal need-to-know, between fashion-conscious and not, between people of all physiques & styles.
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Split focus between “classic” and “current.”
In the span of a week you’ll see Derek Guy post about everything from the styles of decades-old fashion in Greece and the brilliance of Korean tailoring to Elle Fanning’s dress at Cannes and Bruce Willis’ timeless style. Reference obscure icons from all time periods within your niche as well as mainstream celebrities that rule pop culture today. Too much classics and you’re out of touch; too much current and you sound like a gossip column.
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Have some evidence-based hot takes.
I wouldn’t say be controversial for controversy sake, but if you already have a take that could be controversial, say it. If you think dress sneakers are hideous and unsophisticated, say it. If everyone’s wearing low-rise skinny jeans and you think they should be straight-legged and high-waisted, say it. (Ideally support your hot takes with evidence tied to your expertise.)
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Make jokes.
Humor is the key to being consistently likable and avoiding having an uptight persona, especially when you’re becoming increasingly “successful.” Show that you can laugh at yourself and at your own obsession with your craft. Derek Guy meme’s himself and everyone else and generally takes it all in jest.
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Pick fights with the powerful.
Challenge the tastes, choices, arguments of famous or powerful people. Derek Guy often critiques high-status people’s fashion choices. And audiences tend to feel ok about, maybe even enjoy seeing influential figures being critiqued, especially on niche subjects rather than on personal attributes.
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Do Crowd Work
These days, he also does impromptu AMA-style sessions on Twitter. He doesn’t just answer individual questions; he gives generalizable lessons to benefit everyone. This interactive approach creates an even more authentic form of content that educates, entertains, and directly engages the audience.
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Be there every day.
Derek Guy is always around. I rarely go a day on Twitter without seeing one of his posts. This isn’t unique to him, but it’s a big part of making him feel like a familiar friend in the neighborhood.
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Be confident (or act like it).
Whatever your ideas, be confident in them. Don’t think or write or speak tentatively. If you’re not confident, then revisit #1 and #2: become an expert in something and be obsessed with the craft.
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Don’t take shit from people.
Inevitably if you’re geeking out about something and some people start to like you, the haters will come along and want to give you shit for it. If you find yourself in this situation, you need to be able to give shit back — in a way that’s cheeky yet doesn’t make you seem like a jerk but also doesn’t make you seem too soft to handle it. Stand up for yourself, and try to be chill while doing it.
Even if you do these thirteen things, of course, there’s still no guarantee of achieving the same level of success as Derek Guy. In fact, it’s very unlikely you will. Because the “Elon-buys-Twitter bump” only happens once. Not every topic is equally popular either. (Clothing and style have more universal appeal than niche areas like building consumer social apps.) There are intangible elements at play as well—charisma, street smarts, timing, luck, or a mix of all these.
Yet, there’s still much to learn from people who have done new and impressive things, even if you don’t want to do the exact same thing in the exact same way.
Perhaps the most notable feat is how Derek Guy has created such a strong character or persona or whatever you’d like to call it — one that seems to be authentic to himself, his taste, personality, and style. One that feels both relatable and universal yet niche and opinionated at the same time. One that resonates.
In many ways I think this is what we’re all trying to do when we post online, whether on Twitter or Instagram or TikTok, on a YouTube channel, or writing a newsletter or blog like this one. The dream isn’t just to show all of ourselves unfiltered to the world. It’s to find a character that we feel comfortable being, that we deeply resonate with, and if we’re lucky, some part of the world might too.