Outfit advice from menswear’s ‘It-Girl,’ @Dieworkwear



Cody Skinner

If you’ve spent any amount of time online, you may have run into the fashion advice of Derek Guy, or, as he’s known on the Internet, Dieworkwear. Guy has been giving menswear advice for the past decade on his blog and on his 600,000-follower Twitter account. In recent years, though, his influence has spread far beyond the menswear blogosphere.

His ethos is simple: “I encourage people to be more thoughtful about their clothing choices.” In pursuit of this mission, he publishes content on how men of all ages, sizes and backgrounds can pay attention to things like clothing quality, silhouette and tailoring.

Guy spoke with the News about menswear on college campuses and on the history of the “Ivy Style” at Yale.

He began by discussing Yale’s fashion history, which is unique for the role Yale’s student body played in disseminating what would later be called “Ivy Style.” 

Yale Daily News — Sept. 20, 1962

“These campuses used to be populated by people who went through the feeder school system, often privileged White Anglosaxon Protestants from the Northeast,” Guy said.

The Ivy League universities, including Yale, reflected the dress codes of the private preparatory schools that their affluent male students came from.

Clothing trends arose from the students’ relaxed attitudes and included tweeds, loose repp ties, oxford cloth button-downs and flat-front chinos.

“Over time, these campuses have become more diverse in terms of ethnic and class makeup within the United States, but also a larger population of international students,” he said.

What Guy is referring to is the role of legislation like the G.I. Bill and efforts made by the Yale admissions office to increase the University’s socio-economic diversity, which shifted the prevailing clothing focus away from the homogeneous “preppy” and “Ivy” fashion to a more democratic style incorporating clothing trends from where students grew up — now not only upper-class Northeastern towns.

“You can’t expect people to adopt a costume from the 1950s,” he said. “One, that world has long moved on.”

Guy went on to explain how Ivy Style’s popularity was already in decline at the time it was identified in photography books such as “Take Ivy.” 

“That style was dead at the time it was documented, and it’s certainly dead now, both in the temporal sense — the world has moved on — and also in a demographic sense, people could now make up these college campuses from different backgrounds and bring their own natural dress practices,” he said. “And they’re not going to put on costumes for the sake of menswear bloggers.” 

The popularity of Ivy staples, however, did not die, and instead became part of the larger menswear sphere. As college education became more accessible to Americans, the Ivy League look became more accessible, too.

Tracing the look’s history, Guy cited the clothing innovations of Brooks Brothers, America’s oldest clothing brand.

The brand’s fortunes started climbing in the mid-to-late 19th century, coinciding with the rise of industrial capitalism, he continued. 

When the merchant class began to wear lounge suits, it was Brooks Brothers that began designing and importing new clothing to fulfill the cultural menswear demand.

“The things that landed at Brooks Brothers’ Madison Avenue shop became the ABC’s of American dress language,” Guy said. “Whatever sentences you want to write, you still have to use the ABC’s.”

Guy brought up a conversation he had with the founder of Rowing Blazers, Jack Carlson. Carlson, who had attended Georgetown and Oxford, subverts the clothing language of private universities with loud prints and bright colors. 

Guy explained that Carlson observed how today’s youth live in the present and engage with contemporary culture, such as rap music. Jack said that the younger generations are not the aristocratic caricatures they once were, but rather individuals shaped by their lived experiences — which then naturally influence their fashion choices. As a result, they seamlessly integrate Ivy League pieces with popular items like sneakers. 

“Fashion is both you exploring your identity and you expressing your identity,” he said. “If you’re into sneakers, you’re naturally going to wear sneakers.”

When asked about how modern college students could incorporate traditional Ivy League pieces, Guy said, “I would get easy-to-wash, durable items like 5-pocket cords and a Shetland knit — which, to me, is such a versatile, easy piece. I personally think loafers are great, but if you’re trying to update it, maybe you wear it with sneakers. The New Balance 550s are a classic Aimé Leon Dore sneaker. Oxford cloth button downs are easy to wash and easy to maintain.”

Guy emphasized the importance of durable goods, saying, “It’s harder now for a student to wear tailored jackets because they’re expensive and hard to maintain — expensive to upkeep. You’re not partying in a blazer. [Clothes that are] … low maintenance [and] reasonably affordable, you’re not going to freak out if you spill beer on it.”

Guy alluded to the idea of a “Rugged Ivy,” the midwestern counterpart to Yale, Harvard and Princeton’s fashion trends. 

Among the common brands and pieces represented are L.L. Bean, Eddie Bauer, sweatshirts, mountain parkas and Danner boots.

“Rugged Ivy is a lot more practical for a student nowadays than a ‘knit tie blazer’ kind of look,” Guy said. “I would get stuff like that and wear it with stuff that most allows you to express and explore your identity.”

When asked about how modern college students could build the confidence to “dress up,” Guy advised building an understanding of how certain articles of clothing can be more casual than others. 

He noted that white poplin spread collar shirts will look more formal than a light blue Oxford cloth button down — and white and black more so than blue and brown, for example. Guy moreover suggested students to look for rougher fabrics and items that are easier to maintain. 

He went on to discuss the spotlight effect, a term coined by Cornell professor Thomas Gilovich in 1999 to describe the egocentric bias people have in their perception of others’ opinions.

“It’s helpful when you’re trying on different clothes — clothes are very personal, they fit our skin and affect how others perceive us — and if we are wearing something we’re not used to wearing, it can make us very self-conscious, especially if it feels like people might think we’re putting on airs. It’s helpful to keep in mind that this is all going on in your head,” he said. 

Guy also spoke to how some people are worried about coming across as pretentious in their clothing. 

He said that the simplest way to prevent this is to be a down-to-earth person with nice manners. 

“If you’re worried that people think you’re a jerk because you’re wearing a polo or a button up shirt, just don’t be a jerk,” he said. “That’s the best way to counteract that judgment.” 

For Guy, a priority has always been to provide fashion advice for men of all body types. 

Having a build that is less characteristic of a runway build does not mean that one cannot dress well, he said. 

“Something I’ve noticed is that you can put up an image of any garment, and someone will say, ‘Only slim ppl can wear that,’” Guy wrote in a post on Twitter, the platform now called X. “It can be slim or wide pants, low or high rise, or anything unusual. IMO, this view comes from personal insecurity & fetishization of certain body types.”

When asked about his promotion of body positivity, Guy said he doesn’t necessarily make a “conscious” effort.

He has seen men of various physiques “look great” with their fashion choices. 

“Many of the men I admire stylistically are short, heavy-set Italian older men,” Guy said. “They’re old Italian tailors with bad posture who carry a lot of weight from eating a lot of pasta, and they look amazing. I think they look incredibly elegant and incredibly stylish.”

Guy ended the conversation by touching on J. Press, a clothing store founded in New Haven with the slogan, “Definitive Ivy League style since 1902.”

The New Haven branch is located at 262 Elm St. 

Yale Daily News — Sept. 24, 1962

“J. Press has been really impressive because you can’t do what they do at a large scale. Brooks Brothers has become a mall brand because it is a massive company,” Guy said. “J. Press has a few locations whereas Brooks Brothers has hundreds. Brooks Brothers has to pay for leases, and because J. Press is small, they can make, for me, a more interesting look.”

Despite being a heritage brand, J. Press has adapted to the online menswear discourse, amassing over 58,000 followers on Instagram.

In contrast, several contemporary labels such as Aimé Leon Dore, Bode and Rowing Blazers are reinterpreting the Ivy Style for a modern young adult audience, infusing the Ivy League campus’ history with vibrant colors, unconventional fabrics and new silhouettes.

Derek Guy has been published in the Washington Post, Esquire, The Nation, the New York Times, Financial Times and Business of Fashion.

Related Posts