When you think of the sartorial stylings of Billy Crystal, you probably picture the legendary actor in a standard-issue tuxedo—on the red carpet, probably, or even hosting the Academy Awards. Perhaps you think of the movie costume he made iconic: his white fisherman sweater look from the beloved 1989 romantic-comedy When Harry Met Sally, an outfit that has been duly celebrated in recent years. Either way, Crystal isn't quite up there with throwback style icons like Jack Nicholson and Harrison Ford, who usually dominate the menswear mood board circuit. Consider it a happy surprise, then, that back in his day, Crystal's real-world style looks incredible from our current vantage point. In fact, if you look closely, it's hard to ignore the links between his looks back then and some of our favorite menswear of the moment.
Throughout the 1980s and early 1990s, Crystal was everywhere: in movies and television shows and on Broadway stages. He was heavily in the public eye, but he didn't dress with the showy pizzazz of a big-time celebrity. Take a look at this outfit from one premiere party—a loose-knit sweater and tan pants is an advanced-level look—and one that echoes the playful, contemporary vibes of a label like Our Legacy. More often, though, Crystal was in some combination of Levi's 501 jeans, a crewneck sweater, and sporty sneakers. (The 501, of course, is the straight-legged Levi's style that we gave the "best jeans" label...this year.) Whether denim or chinos, though, Crystal knew that the most important thing about your pants was the fit. And his pants did: the just-right relaxed fit, the hem that perfectly hit the footwear—and when it came to trousers, he didn't shy away from a suitable pleat. He could also style the hell out of them: usually dressed down in white sneakers and occasionally with a statement knit sweater. (Not to mention a garment bag from the iconic Los Angeles retailer Fred Segal.)
In his off-duty wardrobe, you got the feeling that Crystal put classic and comfortable staples above any overt notion of fashion. He locked into the idea that all it takes to look good is an excellent pair of pants, a well-fitting sweater, some crisp sneakers—and rarely strayed from it. It feels surprisingly on par with the menswear of today. These days, after a few years of Gucci-induced maximalism and breathless streetwear drops, many men are leaning towards a more matter-of-fact way of dressing. It started slow—relaxed-fit jeans, a pair of loafers, a simple tee with a choice cardigan—but this way of smart, accessible dressing seems to be catching on among well-dressed dudes. This doesn't feel like a rehashing of the chinos and skinny suits era from Frank Muytjens' J.Crew. Some of the quirks of the past few wild-style years have stayed, and that soft touch of fun can be seen in Crystal's yesteryear style as well.
Of course, when you’re Billy Crystal, sometimes the job requires you to stray. And when his day job called for it, Crystal showed up in simple suits and tuxedos for red carpet appearances. Some looked better than others, but they don’t provide quite the same thrill as his courtside Clippers game attire. (Of course, most of us would probably look relatively tame when standing next to the legendary dresser Robin Williams.) You get the sense that Crystal had no interest in being on the same plane as Williams or his other more intrepid-dressing peers. When he showed up on the red carpet, he was there to do a job—to smile and promote the movie. Looking at the red carpet photos from this time, you never get the sense that he viewed it as an opportunity to stunt in some outlandish outfit. And anyway—it’s way less fun to wear a tuxedo than a pair of loose, drapey gray trousers with your favorite white sneakers.
Crystal is a bit of a dark horse for a throwback-style icon. During the 1980s, he became known for playing comedic characters with edgy, pessimistic charm—not exactly the traditional leading-man roles that you’d see from a Nicholson or a Ford. Perhaps that is what makes his era-specific style streak feel so unexpected and joyous. It was there all along, hiding in plain sight—and more people might have noticed the clothes if they were being worn by a more typical movie star. Look at how Crystal was dressing back then, and it's hard not to draw parallels to modern-day style icons—like, say, Jonah Hill. Sure, Crystal wasn't dressing in in-the-know streetwear or endless Prada, but I sense a similar presence of comfort and self-assurance. In their respective eras, both men looked well-dressed and relatable, like a stylish nobody you might see posted up at your local coffee shop.
Similarly, Crystal always seemed to dress just for himself, and that shines through in his outfits. Perhaps the most remarkable thing about Crystal's 1980s style, though? It still feels like something most of us would be happy to wear today.
