Derek Guy of @dieworkwear has a million followers on X and is known for his smart threads criticizing politicians for their poor fashion choices and lamenting the decline in the quality of American clothing, especially men’s clothing, over the past few decades. When he’s not on X, Guy is a San Francisco-based writer and editor, and he recently shared his tips with Fortune for men who want to look good in the office.
“Men’s fashion in general is more fulfilling than it’s ever been in terms of possibilities, but with so many options it’s also harder than it’s ever been to dress well,” Guy told Fortune. “Before, you could go to a good local store and they’d sell you an entire style. Now you have to buy things from all over the place. It’s so much harder to dress well now.”
So what advice does Guy have for those struggling with what to wear to the office? Of course, there’s no one-size-fits-all answer; it varies greatly by field, city, role, and even individual office. But in general, Guy says more men should dress in a way that makes them feel good. That might mean ditching the chinos and down vests and embracing new brands and styles.
“There are very few rules at this point,” he said, adding that it’s easier to take risks with something as simple as changing from a white shirt to a blue one. The potential consequences of bifurcation are the most minor so far.
“If you want to wear nice clothes, you have to accept that you’re going to stand out, but it’s not a big deal,” he says.
How to experiment with your style
According to Guy, one of the things that stops men from trying new things is not knowing where to find inspiration or even what’s available, so for those looking to hone their style, he suggests getting more creative with platforms like Instagram.
If you’re interested in 1980s punk fashion, you might find brands that capture that aesthetic, follow them on social networks, and browse their tagged photo sections. From there, you can find and follow other people who like your style, see who’s wearing other brands, and use the bookmark feature to save the posts that inspire you the most.
“Basically, it’s about building a mental library of images that you like,” he says. “Over time, you might notice that men tend to wear slightly cropped jackets or high-rise trousers, or clothes in certain fabrics or textures. Find words that describe the look you want.”
Then try on one or two pieces in the style that interests you. This doesn’t mean replacing your entire wardrobe all at once, but maybe try different cuts of jeans or jackets to see how they look, he says.
On a basic level, Guy suggests investing in the following: a tailored sport coat (in a color like navy), gray or tan wool pants (swap for chinos or jeans if they’re too dressy for the office), a tailored dress shirt or polo, a textured sweater, and quality leather dress shoes. Outerwear in particular is a good place to invest more money than usual. If you live in a hot climate, high-quality shoes are a good choice.
“Layering makes an outfit look better. A jacket makes your waist look slimmer and your shoulders look firmer,” he says. “It’s just flattering.”
He says it’s important to pay less attention to trends and more to the cultural relevance of the clothing. Adidas Samba is trendy right now, but it also has a long history in the sports and hip-hop communities. Knowing that history means they “will always be cool, because that history is cool.”
“Don’t think, ‘Does blue go with green?'” he says. “This isn’t a science project. Think of it as a cultural language. Fashion is a weird thing in that it’s both a way we express our identity and a way we explore our identity.”
