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.
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.