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These Shirts Were Made for Laughing: Thoughts on Russell Westbrook’s Masculine Challenge

Westbrook’s looking for something. He’s on a journey.

There are moments that leave you certain that fashion is a joke. You look at the clothes and laugh and think, Surely, these guys are aware of the comedy. Surely they know that a cropped sweater and midrise culottes with work boots, a vest, and a bowler cap is too much. The other day I saw a guy walking toward the subway in a black slub-knit T-shirt that reached the middle of his thighs. He wore it over a pair of black genie pants with a crotch that sagged far enough down to make it look as if he were wearing a very expensive udder. It was like a building strutting around town with the scaffolding still attached. Is no one going to say anything?

On an upscale retail site like Ssense, the designer clothing twerks on the border between audacity and “Are you kidding me?” The styling never ceases to entertain, in part because you don’t know what to believe. The models always have the stain of a smirk. They wear black crepe biker jackets and green lambskin basketball shorts. Most of the pieces — from upper-echelon fantasists like Rick Owens, Balmain, Alexander McQueen, Maison Kitsuné, and Ann Demeulemeester — are exquisite. But sometimes they defy description. Telling you, for instance, that Demeulemeester has an ecru, sheer, striped, hooded button-down shirt (black stripes on white) misses the shirt’s essential blouse nature — that the man wearing it is destined to resemble a major actress during her juice lunch at a hot restaurant.

These are pieces that work in the showrooms and on the runways and in the abstract, but need charisma and belief and the right body to work on the street. They need somewhere to go. And what happens when they don’t have a somewhere? I’m reluctant to ask this question of Russell Westbrook, who has been generous with his attempts to tackle the enduring conundrums of couture menswear in the social sphere. He’s been putting on clothes and having someone take a picture. The results live in his Instagram feed, which, for him, is the archive of a sports star boldly going where no one else in the NBA has recently dared. We’re talking overalls cuffed at the bottom with the bib turned down, say; or a tailored, floral-print sleeveless tunic over white, lightweight, ban-cuff leggings with a dropped crotch. The post of the tunic has been “liked” more than 26,000 times, which means there are a lot of people fond of men who look like instructors at the Barneys Co-op SoulCycle class.

Westbrook wore that to last year’s Teen Choice Awards, where he was photographed with the rapper Nelly, who wore a Mentos-green T-shirt, quilted leather shorts, and sneakers the color of a dozen melted ice creams. Posed next to Westbrook, he also wore a face that asked, “Would it have killed you to put the sleeves back on that shirt?” But that’s where Westbrook has been for the last three basketball seasons: Yes, it would have killed him.

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The NBA line for “out there” is Westbrook. It used to be Dennis Rodman in that role, although that was a more archly subversive proposition. A generation later we had LeBron James, Dwyane Wade, and, to a less convincing extent, Amar’e Stoudemire, men who bent the dress code until it seemed to lose its shape. At 25, Westbrook is only four years younger than James, but those four years constitute a generation in sports. He looked at his peers at the vanguard of style and yawned. There was some legitimacy in that boredom. Those guys had stylists, which is the style equivalent of Auto-Tune. Westbrook proudly styled himself. And for a while, he’d found something: prints. Very good ones. In 2012, during the playoffs, he wore big red costume glasses and a white, long-sleeve Prada button-down with a bright jump-jive-and-wail pattern. The outfit made him a star. He followed it up with more smart, decently tailored pieces that, on him, said, “Hey, the ice cream man is coming,” and, “Mommy, these are my favorite sheets.” Most of the time, his nerd-bro-skate-rapper boyishness didn’t seem to be in any kind of conversation with the work-wear variations worn by his peers at the top of the league. Every day was casual Friday with Westbrook.

But it’s not far from there to casualty. Eventually, simple pieces turned into whole outfits, and whole outfits turned into looks, and some of the looks turned out to be one-alarm fiascos: tight windowpane pants, suspenders, tiny bow tie, dress shirt with rolled-up sleeves, trilby hat, big plastic frames. At press conferences, he went further. In November, he wore a black sleeveless hoodie with a gold chain and medallion on top. It was very “I hate Warner Bros.”–era Prince. He’s arrived at games with the pants legs pushed above his calves in a way that made you nervous for his circulation. That’s the thing about a lot of these clothes. They don’t look comfortable on Westbrook. In professional basketball, he’s of below-average height. In the real world, he’s tall. But his arms and shoulders have sculpture, so in some of his more ornate concoctions, with glasses and hats, he’s like a superhero doing a bad job at hiding. Westbrook’s looking for something. Again, he’s 25. There are men who never find clothes that both flatter them and tell a story. He’s on a journey.

That journey has brought him to New York. Westbrook attends Fashion Week events, and, depending on whose shows and parties you go to, you can leave either inspired or deflated. Westbrook has become inflated. He’s making choices and seeing if they work, at least in the eyes of people prone to pressing “like” on a smartphone screen. But his interest in seeing how some aspect of the industry works and his general flair has won him admirers from fashion’s Olympus. He’s watched shows next to Anna Wintour and has received plaudits from Richard Chai. It feels a little like gods humoring an arriviste. In a flattering New York Times story on Westbrook, Jill Demling, the entertainment editor of Vogue, referred to him as the “Kate Moss of the NBA.” If you don’t think too hard about what’s wrong with the comparison, a first inclination is to blush. Then you remember this is a league in which some well-dressed men look like Jamie Foxx’s Wanda.

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Westbrook appears to be dialing things back. After a loss to the Spurs in Game 2 of the Western Conference finals, he greeted reporters in a black porkpie hat and matching zip-up vest over a relatively loose-fitting green T-shirt. During the press conference after Game 6, it was a Hulk-green half-sleeved number with no accessories. After a terrible loss, you’re just not in the mood for style. But the Instagram feed also reflects some kind of restraint. Westbrook’s sense of style meets up with the willful androgyny of musical acts like Le1f and Stromae, men who luxuriate in trolling virility. Some people take the bait and shake their heads. I don’t think Westbrook means to go as far those two, but all three represent a conscious thumbing of the nose at the masculine status quo. And that freaks people out. It gives them a case of the Rodmans.

It’s just that, with Westbrook, you imagine one goal of that radical challenge is to look good, too. He looks best in photo shoots, where he’s clearly collaborated on the clothes and styling. Or he’s left it to someone else and winds up seeming in command of the accessorizing and colors. There’s no joke in most of those magazine shoots, just an athlete’s persuasive self-expression. He’s a basketball player, after all. Style-wise, he might be better off with a team, because there’s a difference between working with a stylist and working against yourself.