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Derek Guy, Twitter men’s wear expert, offers his best fashion advice for men in the workplace

Jun 17, 2024

Derek Guy—better known as Twitter’s “men’s wear guy”—would rather men wear “chicken suits” to work than the current business casual trend: blue dress shirt, slim low-rise chinos, a Patagonia vest, and a pair of dress sneakers. 

“It’s a really ugly aesthetic,” Guy told Fortune.

The ensemble—which some have called the “finance bro outfit”—is vanilla, shows little personality, and is not flattering to the body, he said. 

Those who have recently spent time on X (formerly Twitter) might not be initially surprised by Guy’s take. The Canadian-born, California-based style blogger has accrued nearly 1 million followers on X by needling politicians and celebrities for their fashion choices. Many X users, beyond the typical fashion critics, have read Guy’s sartorial advice after he inexplicably shot into virality last year.  

However, Guy is not the formality-obsessed hater that his critics make him out to be. Rather, he wants men to wear clothes that make them feel gratified, and good, instead of putting on the same uniform for work every day. 

“We live in a time where there are more options and more freedom than ever,” he said. “It’s just that many guys don’t take advantage of it.” 

Most finance bros don’t take joy in their button-ups and chinos, Guy believes, because they’re not meant to look good; it’s just the perfunctory outfit, something you put on to look respectable. Men fear that stepping outside those norms could lead to teasing, looking unprofessional, or appearing too formal or stuck-up. 

Guy dismisses those fears. In the post–work-from-home era, where office culture is navigating new norms of casualness, we’ve landed on the “ugliest” version of the business casual aesthetic, he said. Men still want to look formal, but are afraid of sticking out.

“I would rather you put on clothes and be like, ‘I feel awesome,’” Guy said.  

How should men navigate the new, casual office culture, while also looking good? The answer, Guy said, begins with a tailored sport coat. 

Start formal, then move down

“Try as hard as you can to incorporate a tailored sport coat into your attire,” Guy said. The piece gives men a silhouette with broader shoulders and a slimmer waist, which is flattering, he added. 

How do you style a sport coat? Men should try a classic, formal work outfit, and then adjust elements of the outfit based on office culture, Guy said. 

The classic outfit he suggests is an oxford cloth button-down, layered under a navy sport coat, with gray wool trousers and leather dress shoes. 

Many men may find that too formal for the office, Guy said. So exchange the trousers for chinos. If that’s still too dressy, try jeans, a long-sleeve polo, and simple white sneakers rather than dress shoes. 

If the sport coat still feels too dressy, try a shirt with some texture. For the winter, a textured sweater: an Irish fisherman, cable-knit, or Shetland knit. In the summer, a Johnny collar polo, camp collar shirt, or a T-shirt with a cardigan is “much more interesting” than a button-down. 

Men can find inspiration in brands, or in other businessmen who have good style, Guy said. Classic brands like J. Crew, Todd Snyder, and Buck Mason excel at providing alternatives to dress shirts, he noted. 

One man who has mastered nice-looking business casual is Adam Mosseri, head of Instagram, Guy added. Rocking cardigans, polos, and T-shirts with a sport coat, Mosseri is Guy’s style icon for the new return-to-work men’s wear. 

However, if after trying the new shirts it doesn’t feel as right as the dress shirt—fine, Guy said, but at least make it fit well. He recommends the online shop Proper Cloth, which designs custom-fit, made-to-order dress shirts that are pricey but worth the cost.

Stop wearing skinny chinos

Think about how to dress to best flatter your body type, Guy said. 

“A lot of guys are squeezing into these really slim fit chinos that don’t flatter them,” he noted. “It doesn’t mean that nobody should wear skinny pants, but skinny pants have to work with the aesthetic, and they don’t really work with a business-professional aesthetic.” 

Aim for a trouser that has a slightly baggier fit, so that your silhouette looks more rounded out, Guy said. 

It’s easy to test if your pants are too small, Guy added. Look at yourself in the mirror, and if your hip pockets are flaring out, the pants are too tight across your hips. If the pants are wrinkling across your lap, they may be too tight on your legs. If you catch a three-way-mirror, check out how your pants fit across your legs. If they’re causing ripples down the back, that’s another sign the pants are too small. 

“When you get the fit right and things drape well, they look better,” Guy said. “Versus when guys are squeezing themselves into these tight shirts, they end up constricting, and it doesn’t flatter you, and it doesn’t feel comfortable.” 

Above all, wear the leather jacket, or whatever makes you feel the best

There’s another route Guy would prefer that finance bros follow: Wear whatever you want, including a leather jacket, à la Jensen Huang, Nvidia’s CEO. 

“Huang dresses pretty stylishly,” Guy said.

If we allowed a true-blue casualness in the office, which could include trucker or leather jackets, “that would be better than forcing everyone into this business casual, that neither has the flattering effects of tailoring nor the creative expression possible for casual wear,” he added. 

In a world of Bill Gates’ T-shirts and Huang’s leather jackets—a world in which we have forgone long-held notions of respectability—we might as well move beyond judging people on their clothing, he said. In the workplace, someone wearing a T-shirt should be expected to do the same quality of work as someone in a suit. 

“A lot of guys are so scared of exploring, that they assume that if they wear the wrong jacket, something bad’s gonna happen,” Guy said. “I don’t think the world’s that bad.”

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