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You Should Dress Like Weezer on Letterman in 1995

GQ 3/17/2023 Yang-Yi Goh

You Should Dress Like is a recurring column in which GQ writers profess their love for hyperspecific moments in celebrity style, and then show you how to bring those vibes directly to your wardrobe.

On August 4, 1995, Weezer rolled onto Late Show with David Letterman at something of a crossroads. The band's self-titled 1994 debut was, by that stage, a platinum-selling phenomenon—but the weight of that success had taken a toll on frontman Rivers Cuomo. Sick of “playing the same ten songs every night,” as he'd later tell Rolling Stone, Cuomo decided to enroll as an undergrad at Harvard—he would begin his freshman year shortly after this performance, leaving the rest of his bandmates somewhat stuck between stations. Meanwhile, earlier that summer, Cuomo also underwent a painful procedure to lengthen his left leg (it was 44 millimeters shorter than the right), which required him to wear a clunky metal brace for months. 

All of that mental and physical distress resulted in one of the oddest, most deeply affecting performances in late-night TV history. “Say It Ain't So,” the third single off Weezer's first LP, was already an oddity in the quartet's then-limited oeuvre—a heavy, heartrendingly personal ballad on an album full of power-pop confections. But on Late Show, amid all the uncertainty over the band's future, the song crackled with an even fiercer, almost unsettling electricity that still has the power to shroud your arms in goosebumps. 

Beyond the music itself, there's a lot to notice and love in this video—from Letterman's goofy “Weezer/Tweezer” joke at the top to bassist Matt Sharp's epic power stances. Of course, because I work at GQ, the thing I tend to focus on most is what everybody is wearing. The clothes are somehow both extremely of the era and totally timeless, and every outfit speaks volumes to who that person is and what they're going through in this particular moment. Let's take a closer look at each individual ensemble.

Rivers Cuomo

© GQ

By this stage, Cuomo had shed the geeky, hipster-y signifiers—the retro soccer jerseys, shaggy bowl cut, and horn-rimmed glasses—that had become his trademark. He was going through it, and his subtle style reflected that. On Late Night, he donned a plaid shirt—but it was a muted, lightweight button-down, as opposed to the beefy flannels favored by grunge kids at the time. To hide his leg brace, Cuomo pulled on the baggiest khakis he could find, a move straight out of the J.Crew playbook circa 2023

There's a quiet power to Cuomo's fit here. It's lived-in and unaffected, and allows his raw, unfiltered emotions to take center stage—as they soon would again on Weezer's 1996 sophomore record Pinkerton, an early emo masterpiece. The initial commercial and critical failure of Pinkerton would eventually, in the early 2000s, drive Cuomo to attempt to exactingly engineer every aspect of his life: he kept massive binders full of equations through which he tried to devise the perfect pop song, and he hired a stylist to put together a handful of anonymous suit-and-tie combinations he could rotate through thoughtlessly for public appearances. But in the summer of '95, on Letterman’s stage, Cuomo was still dressing himself with an admirable and palpable authenticity—favoring the kind of easy, effortless clothes you should always have on hand for sleepy Sunday strolls and relaxing weeknights in. 

© Provided by GQ [article/slideshow]

Brooks Brothers poplin Friday shirt

$90.00, Brooks Brothers

© Provided by GQ [article/slideshow]

J.Crew giant-fit chino pant

$98.00, J.Crew

© Provided by GQ [article/slideshow]

Converse CONS PL Vulc Pro Suede skate shoe

$75.00, Converse

© Provided by GQ [article/slideshow]

American Trench retro stripe socks

$14.00, Huckberry

Matt Sharp

© GQ

Truthfully, this look is the main reason I wanted to write this story in the first place. Nobody has ever looked radder on national television than Matt Sharp does during this performance. A lot of that has to do with his caustic energy, leaping about and slamming his battle-scarred bass into oblivion. (Sharp would later say he tried to play big to draw attention away from Rivers' noticeable lack of mobility.) But it's also because of his righteous, supremely 1995 fit. 

There's the era-specific long-sleeve-under-short-sleeve layering technique—a foolproof way to tell the world “I like music”—done here with extra finesse by way of a throwback graphic ringer tee over a fitted turquoise undershirt. On his lower half, Sharp kept things simple with two timeless skateboarding staples: slightly cropped Dickies 874s and beat-to-hell Vans Authentics. He pulled the whole look together with a pair of oversized frames—which he'd later wear to great effect on a 1997 album cover for his side project The Rentals.

If Cuomo was Weezer's ego, Sharp was its id: all jagged edges and larger-than-life presence, providing a necessary counterweight—through his throbbing baselines, backup falsettos, and vibey clothes—to his frontman's straight-ahead songwriting. Some Weezer fans believe the band lost its soul upon Sharp's departure in 1998, and while that's debatable musically, it's absolutely true sartorially: Never again did one of its members display such singular personal style. 

© Provided by GQ [article/slideshow]

Y,IWO ringer printed cotton tee

$60.00, Mr Porter

© Provided by GQ [article/slideshow]

Gildan Ultra cotton long sleeve T-shirt

$16.00, Amazon

© Provided by GQ [article/slideshow]

Dickies original 874 work pant

$30.00, Amazon

© Provided by GQ [article/slideshow]

Vans Authentic shoes

$60.00, Zappos

Brian Bell

© GQ

Of everyone in the video, rhythm guitarist Brian Bell is dressed the most like a dude you'd see in Brooklyn bar circa 2023: loose white camp shirt, flared black trousers, shiny black boots. Much like Bell himself, the look is quietly cool and highly effective. 

(Quick word of advice: If you're going to cop the Wrangler pants we recommend below—which, at just $26 a pop, you absolutely should—they run infamously small, so go up at least two sizes from your regular waist.) 

© Provided by GQ [article/slideshow]

Bather lightweight cotton camp shirt

$150.00, Saks Fifth Avenue

© Provided by GQ [article/slideshow]

Wrangler Wrancher dress jean

$26.00, Amazon

© Provided by GQ [article/slideshow]

Our Legacy black leather belt

$175.00, SSENSE

© Provided by GQ [article/slideshow]

R.M. Williams classic RM leather chelsea boots

$432.00, Amazon

Patrick Wilson

© GQ

If you've ever watched an interview with Weezer dummer Pat Wilson, you'll know he's an absolute teddy bear with a killer wit. But his Late Show look is pure '90s hardcore kid: tough-as-nails work jacket, heavyweight chino shorts, and browline glasses, all topped off with a neon green buzzcut. 

© Provided by GQ [article/slideshow]

Everlane filled canvas jacket

$168.00, Everlane

© Provided by GQ [article/slideshow]

Buck Mason Field-Spec cotton heavy tee

$55.00, Buck Mason

© Provided by GQ [article/slideshow]

Carhartt WIP Master short

$115.00, Carhartt WIP

© Provided by GQ [article/slideshow]

Matsuda M2048 glasses

$615.00, SSENSE

David Letterman

© GQ

When people reference David Letterman as a style god, they generally point to two specific periods of his life. There's the young, subversive, ‘80s-era Letterman who remade late-night TV in a sport coat and Sambas. And then there's present-day Letterman, thriving in retirement with a big beard and even bigger waders

But as far as I'm concerned, everybody's sleeping on his early CBS years, when a more established Letterman began sporting dark, double-breasted suits. When Letterman jumped time slots from 12:30 to 11:30 in 1993, he also swapped his tiny 30 Rock studio for the historic Ed Sullivan Theater. His longtime costume designer Susan Hum convinced him it was time to give up his off-the-rack blazers and kooky accessories for something a little more grownup. “There's no more white socks,” Hum told the Chicago Tribune in 1993. “I said: 'Dave, you can't wear those socks with a suit. First of all, we're on a stage now. You're performing for an audience. Wear the black.' ”

Hum designed a series of suits expressly for Letterman and had them crafted bespoke by a reputable New York tailor. They featured elegant, elongated jackets that emphasized his physique, and high-waisted, inverted-pleat trousers that invoked Old Hollywood and allowed Letterman a greater range of movement onstage. He wore them primarily with stark white dress shirts, classic loafers or oxfords, and ties with larger patterns that would show up clearly on television. Letterman's new suits neither stifled nor felt at odds with his outsized personality—instead, like all great tailoring, they emphasized his best qualities by helping him appear even more naturally comfortable and confident than before. 

“He once said that he didn't feel he was going to work unless he was dressed up,” Hum said. “That makes him get into the mood of his show.” Thirty years later, as I continue to ease back into post-pandemic office life, that sentiment rings as true as ever. And more and more, Letterman's distinctly '90s semiformal attire—the graceful tailoring, the crisp white shirts, the legible neckwear—feels like exactly how I want to dress for work everyday. 

© Provided by GQ [article/slideshow]

Kingsman Harry's Super 120s wool suit

$2495.00, Mr Porter

© Provided by GQ [article/slideshow]

Kamakura New York slim fit spread broadcloth shirt

$110.00, Kamakura

© Provided by GQ [article/slideshow]

J.Crew Italian silk tie

$80.00, J.Crew

© Provided by GQ [article/slideshow]

Morjas plain toe blucher shoes

$350.00, Morjas

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