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Katie Holmes cuts a chic figure in white blouse with jeans in NYC

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The internet has, through a deluge of fan-created Instagram accounts and viral screencaps, crystallized an impressively large number of shows from the ’90s as fashion history artifacts. There are the obvious favorites: Sex and the City, The Nanny, pretty much anything Jennifer Aniston wore on Friends. But there is one show from that perennially trendy decade that, after a sorely belated first watch, I strongly believe deserves induction into the 90s fashion canon.

Will & Grace.

Okay. I know, I know. Will & Grace has not exactly aged gracefully (pun intended). It was a flawed show from the get-go, thanks to the lack of diversity, lazy and offensive jokes, etc. The friendship sitcom first premiered in 1998, and was the first network series to have a gay man as its protagonist. It aired amidst a daunting fight for marriage equality and a ban on openly queer people serving in the military.

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Thankfully, things have changed. (Even if the progress feels incomplete and tenuous as anti-LGBTQ legislation crops up across the U.S.) From a modern vantage point, a silly sitcom that relies heavily on simplistic stereotypes and rarely showed its queer male characters, you know, kissing other men, can feel passé. But one part of the complicated series that resonated with me? Will’s impressively strong wardrobe of minimalist 90s menswear.

  Why I’m Dressing Like Will Truman This Summer © Courtesy of Getty Images

Menswear interpretations of ’90s minimalism—that trendy wave of neutral Jil Sander skirts and Calvin Klein suits—seems to have gotten completely lost or forgotten about by 90s enthusiasts. Once upon a time, cream turtlenecks worn under boxy blazers and loose bowling shirt paired with relaxed trousers filled country clubs and hip bars alike. People dressed boring on purpose. (As a 1998 Vanity Fair article on 90s wealth observed, “So coldly austere are the new designer stores—Giorgio Armani, Polo Sport, Calvin Klein, Prada, Dolce & Gabbana, Valentino—that they seem to eschew the very notion of luxury.”)

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But when contemporary brands like Supreme or Aimé Leon Dore turn to the decade for inspiration, they tend to take the casual and streetwear trends. The overalls, bootcuts jeans, and oversized jerseys of the ’90s have overshadowed the deep v-neck sweaters, silky shirts and moto jackets.

Which is why watching Will trounce through eight seasons in a collection of clean, sleek outfits felt delightful for this new Vogue writer. Perhaps part of my attraction to Will—a well-off, neurotic lawyer—is how his deceptively plain looks operate as an antithesis to the maximalist, color-heavy direction today’s fashion is heading in. During Will & Grace’s heyday, menswear religiously stuck to neutrals. Calvin Klein, Armani, Helmut Lang, and Brooks Brothers were the definition of Manhattan cool. Some other great examples from the era of quiet luxury include Ryan Phillippe in Cruel Intentions and Christian Bale in American Psycho. There was an art to simplicity.

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  Why I’m Dressing Like Will Truman This Summer © Courtesy of Getty Images

Of course, Will Truman’s outfits go beyond being easy on the eyes. They are a reflection of his character and, inadvertently, a reflection of what LGBTQ+ lives were like in the 90s. (Okay, well, what life was like for a very specific slice of the community.)

Will’s character is out and proud, but he is often positioned by writers as “straight-passing” at times. The series is full of jokes that Will and Grace pass off as a couple and Jack, a theater geek and Will’s close friend, acts as the flamboyant counterpart to Will.We are more likely to see Will grabbing dinner at a trendy restaurant with Grace, than him partying it up at a grungy, queer East Village bar. And he feels miles away from the explicitly queer fashion on display in Madonna videos and documentaries like Paris is Burning. This leads me to believe Will’s wardrobe is that of someone concerned with heteronormative respectability and assimilation. That makes sense for the era. In one episode, shortly after Grace elopes on a whim, Will bemoans that he will never experience the same milestone: arguing that commitment ceremonies, which are not legally binding and lack the legal protections of marriage, pales to a wedding.

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  Why I’m Dressing Like Will Truman This Summer © Courtesy of Getty Images

This captures an era of activism. I can easily imagine a host of well-to do queer men like Will, in the 90s, deliberately turning to muted power dressing as way of blending in, in a world where they easily stood out.

Today, menswear is in a very different, and more expansive, place. Just look at the bold, chromatic outfits by Kim Jones at Dior Mens, J.W. Anderson, and ERL.. Of course, I’m not seeing these looks on lawyers and finance bros walking around downtown Manhattan during the week. But during the weekend, in Brooklyn, a neon-hued short-short feels like appropriate attire for the fashionable and the non-fashionable, queer and straight.

Which might be why I’ve honed in on Will’s conservative dressing and begun wishfully constructing online shopping carts with items that embody notes of 90s minimalism. I like to zig when the world zags and the contrarian in me might just be turning away from the look-at-me! aesthetics dominating fashion. I want to blend in. At least for a little bit.

  Why I’m Dressing Like Will Truman This Summer © Courtesy of Getty Images

To tap into Will’s style, I’ve been looking at elevated streetwear-flavored brands—in order to keep at least one foot in 2022—like the California-based label Second/Layer and Aimé Leon Dore. The clean—dare I say almost sterile—palettes Matthieu Blazy played with for Bottega Veneta’s spring 2022 collection also fit the bill. And I recently paid a visit to the Chicago flagship Ralph Lauren store and walked out with some bootcut surplus trousers that I could imagine Will wearing on a quick coffee trip.

9 Fantastic Experiences In The Wild Town Of Darwin, Australia

  9 Fantastic Experiences In The Wild Town Of Darwin, Australia Visit Darwin, Australia, to swim with crocodiles, watch a beer can boat regatta, and immerse yourself in Aboriginal art.Encased in a transparent plastic “cage,” I watched as the giant saltwater crocodile circled around me, its massive body barely making a ripple in the water. With a 3-ton bite force, this ancient creature is the ultimate stealth hunter — and I was in the water with him in the aptly named “Cage of Death” at Crocosaurus Cove in the Northern Territory city of Darwin, Australia.

I’m not sure when my Will Phase will come to an end and I pull out the trendy charm necklaces and baby tees back out. But for now, it feels good to tap into the minimalism of a bygone era and scale back.

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