There he was, in head-to-toe black on David Letterman’s couch, joking about the police sting that outed him and his sex life to the whole world. George Michael might have been embarrassed in 1998—anyone might have, even in 2019—that an arrest in a Los Angeles public bathroom became fodder for every comedian on earth, but when he appeared on late-night TV to address the issue head-on, he looked so damn dignified in a three-button blazer and slightly flared trousers that it made explicit what we already knew deep down: that there was nothing to be ashamed of. That even if you are outed against your will, you can do what gay men have always done in the face of adversity, which is navigate a treacherous world with a cool sense of style.
Of course, Michael once sang, Sometimes the clothes do not make the man on his liberation anthem “Freedom! ’90.” But he knew that clothes really matter, for good and for bad. In the early part of his career (the Wham! era), hot shorts, highlighted hair, and neon colors made him a heartthrob. As he matured and went solo in 1987, he showed us, through donning more tasteful clothes, that he had escaped teen-dream hell and grown into an artist. By his mid-20s, he could do a lot with just a pair of tight jeans and a T-shirt. He also began to incorporate subtle elements of high fashion into his wardrobe, like deconstructed blazers that call to mind Giorgio Armani and Yohji Yamamoto.
His outfits always held clues to his private life, for those of us who were looking: the red AIDS ribbon on his lapel, the campy Christian-cross earring that dangled from his ear, the burly chest hair. But when you reflect on his style across the years, it’s striking how timeless and accessible much of it is. It’s always good to rock Levi’s 501s with black leather, to keep your color palette simple and tuck a trim T-shirt into your pants, to load up on beautiful accessories like belts and earrings and rings and let them do the heavy lifting.
In retrospect, it seems obvious that key elements of his style—the sunglasses and hats, the oversize blazers and jackets, the wide-leg trousers—were as much about discretion as expression, a way to protect himself from a public eager to see every part of him laid bare. Which is what he showcased on that late-night couch in a quiet but powerful outfit more than 20 years ago: You and only you get to decide how to look when you walk out into the world. To show only what you want to show. And even when they try to drag you down, you can always dress up.
A version of this story originally appeared in the June/July 2019 issue with the title “The Totally Fearless and Gloriously Free Style of George Michael.”