Looking back, the personal style of the Late Night Wars era, when David Letterman, Jay Leno, and Arsenio Hall battled it out for rating supremacy in a post-Johnny Carson landscape, has aged unusually well. It's not strange to see snaps from the period on Instagram: Letterman and Hall in the bigger suits that we’ve seen make a comeback in recent years, or Jay in his sneaky-cool Canadian tuxedos. But the most stylish host in the Late Night Wars was a fictional one.
When it made its premiere in August 1992, The Larry Sanders Show imagined itself in the middle of the whole late-night battle. It was a famously meta bit of TV-making: star Garry Shandling, who played the eponymous host, had actually guest-hosted The Tonight Show from time to time when Johnny Carson needed a night off, and was asked to take over Letterman’s 12:30 Late Night spot when Dave inherited Carson’s chair. Shandling decided on another idea: a fictional show about a talk show host—one, at that, who often talked about what real-life hosts Dave, Jay, and Arsenio were doing. And in order to pull that off, he needed the look. Larry’s suits for the show feel indebted to Dave, while the set feels a little more Jay (which makes sense, since Larry’s show, like Jay’s, was filmed in L.A., while Dave did his show in New York), with a nod to Johnny’s old set with vegetation behind the desk and guest seats. The show really came to life, though, when it focused on everything that happened in the 23 hours Larry was off the air—and everything about his vibe, 30 years later, has aged beautifully.
Start at home: if it was real, Larry’s house would probably have been remodeled a decade or two ago, but what we see of it screams Best of the Best, Circa 1990. From the looks of it, he’s in one of those perfect old Spanish colonial revival homes from the 1920s or ‘30s. The mood inside is chill, muted, and natural.
Much like his house, Larry—and Garry—maintained a very specific, surprisingly sophisticated casual look. Shandling grew up out west, in Arizona, before moving to Los Angeles, and he dressed like somebody who never spent his formative years wearing clothes to protect him from the cold. In this regard, he was basically a West Coast version of Jerry Seinfeld, except better. Seinfeld is often heralded as the pioneer of done-to-death “normcore” style, which is just a way of saying that he looked content with his style choices. Jeans, sneakers, and an oxford wasn’t an outfit, really—it was just what he wore. (That Jerry was still so vain about his outfits sealed the joke.) Rewatching Larry Sanders and looking at old photos of Shandling, I can’t help but think that, in contrast, he really took his clothes seriously. Shandling was also a fan of the jeans and white sneakers thing, but also played around with tailoring more. Sometimes it was a blazer that looked so good, you thought he had it made specifically to go with a pair of jeans. And whenever it dipped below 75 in L.A., he managed to have a nice long coat ready.
I mention the normcore thing because, even though the term has been kicking around for about a decade now, we still haven’t quite moved on from the influence of normal style. New Balance is as big as ever, and every business has figured out that a new way to generate revenue is to make dad hats. Normcore is no longer a quirky sub-genre of style—rather, its influence has fully embedded itself into the way we dress. It isn’t quirky or out there to wear something like you’re a dad on a network sitcom in 1992—that’s just sort of how everything is these days. It’s also why Shandling (and Shandling-as-Sanders) is the perfect antidote. His whole thing was casual…but not too casual. Fun, but not childish. Put together, but not serious. It fits into a broader reevaluation of the style choices of funny people from the 1990s. Perhaps you've noticed that guys like Chris Rock and Bob Odenkirk always had a handle on what they were pulling out of their closets, and Adam Sandler is now a style icon.
In Shandling’s case—and this extends to his fictional talk show host character as well—it’s hard to not look at what he wore as part of a larger, evolving philosophy, part of his own attempt to grow as a person through Buddhism and Zen meditation. As shown in The Zen Diaries of Garry Shandling, the lovely documentary that came out two years after his passing in 2016, Shandling thought, and often over-thought, about everything. So when you look at pictures of him throughout his career, from his early stand-up to the Larry Sanders precursor, It's Garry Shandling's Show, into the 1990s, you see an evolution that makes sense. He was always stylish but comfortable—the fits a little looser, tailored shirts that he wore with a few buttons undone and no tie, and he obviously had a thing for sneakers. And it really sang because of the way it cut against his perpetually uncomfortable persona. And that’s what I love about Shandling’s looks: he was uncomfortable. He was unsure of himself, even at the highest points of his career. But, as far as I can tell, he was comfortable and certain of the things he wore. That comes through even 30 years later.