The improbable comeback of the leather blazer has been in the works for a few years now. You could point the finger at a few sources. Balenciaga designer Demna Gvasalia and his obsession with good-bad American normcore. An oddly chic Adam Sandler running around the diamond district in Uncut Gems. In due time, this very magazine was dishing on how to find your very own leather blazer—and now Kanye West has been photographed in a slouchy number with increasing frequency.
It’s hard to think about a leather blazer without thinking of stand-up comics of the 1990s. (And Anthony Bourdain, of course.) Comedians and stand-ups of yesteryear uniquely embraced the look: you’d see it on late-night shows and HBO specials alongside other more eccentric-leaning fashions. And while comedians have never quite been thought of as a stylish group, it turns out the ’90s stand-up circuit is chock-full of clothes that have been similarly embraced by today’s more adventurous dressers. Looking at decades-old photos of comics and the like, and the overlap between then and now is hard to miss. Leather pants and berets. Tinted glasses and fuzzed-up sweaters. Slouchy blazers of all sorts. The fashion Venn diagram of today’s downtown scenesters and hip ’90s comedians is basically a circle.
When it came to just-right slouchy suiting, you could count on both Chris Rock and Pauly Shore to nail it. These cuts are best described as “elegantly loose,” and they’d fit right in with today’s most stylish tailoring. Before Jon Stewart became a household name on The Daily Show, he could wear the hell out of a similarly relaxed-fit suit. He wasn’t afraid of the aforementioned leather blazer either. Both Rock and Shore had other sartorial tricks up their sleeves, too. Rock could go charmingly grungy and still look great—like a modern-day Channing Tatum—in baggy jeans, leather jacket, and cap from one of the O.G.s of streetwear, Fuct. Shore was known for flashier fare, hitting the red carpet in everything from animal prints and leather pants to a Demna-level oversized blazer.