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

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