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Chris Pine’s Disastrous ‘Poolman’ Fashion Is Actually Making Him Hotter

Pine has made a name for himself as one of Hollywood’s most creative fashion innovators. With his out-there looks in his new directorial debut film, “Poolman,” he outdoes himself.

Friends, I might have a problem. Give me your thoughts on this one: Is it just me, or is Chris Pine slowly ascending to a plane of hotness that most of us cannot even fathom?

Every time I see a photo of this man, his beard has gotten bushier, his shorts have gotten shorter, and his sartorial sensibilities have grown more outlandish. While most celebrities keep their street style in a fashionable safe zone, Pine likes to leave the gym in rainbow cardigans, PBS tank tops, and woven loafers. Now, he’s given us Poolman—his directorial debut in which he also stars as a man who dresses like he found all of his clothes abandoned on some dock while random couples skinny-dip. Maybe it’s the recovering Floridian-turned-Brooklynite in me, but I swear I’ve never seen an aesthetic so appealing in my life.

If there’s one thing I’ve learned during my thirty-something years on Earth and my decade as an entertainment reporter, it’s that being fashionable has little to do with taste and everything to do with confidence. The line between fashion monster and fashion roadkill is often as simple as how high a person is able to hold their head while they strut.

Pine is a perfect example of this phenomenon. On one hand, yes, he has an undeniably sharp eye for colors and patterns—just look at some of his finest red carpet outfits from the last few years, including that red velvet jacket and pussy-bow blouse combo he wore to the Vanity Fair Oscars party in 2022. On the other, his post-workout ’fits break pretty much all the rules. And yet, no matter what this man wears, including short shorts and hiking boots on the red carpet, I find myself utterly entranced—hypnotized by the confidence, the calves, the sheer courage of it all.

In Poolman, a bizarre comedy-mystery, Pine basically expands on this aesthetic to craft an entire character—the amateur sleuth Darren Barrenman. Like a chaotic boy room, Darren’s wardrobe feels like a gorgeously cobbled-together mishmash of aesthetics and detritus—a beat-up straw bowler here and a Big Boy tank top there, with a gold kimono thrown on top for good measure. At one point, in what can only be described as a zany fashion chef’s kiss, he shows up at a woman’s door in a white pussy bow blouse, black trousers, a black vest, and a black brimmed hat and greets her with the words, “This is my take on Cary Grant.” No notes!

The outfits in this film are completely in keeping with the eccentric dress style that Pine has made his calling card for the past few years. Darren often wanders around in some combination of faded swim trunks, old tank tops, and mismatched fingerless gloves. Sometimes his long, shaggy hair is falling around his face, and sometimes he’s pulled it back into a half bun. His idea of court attire is a tan linen blazer, big black shades, an “I <3 L.A.” T-shirt, and black denim shorts. (As one might’ve predicted, jorts abound in this film, as do brown hiking boots and brimmed hats.) Somehow, it feels appropriate that Darren owns more matching pajama sets than he does actually composed daytime wear.

Those who’ve kept a close eye on Pine’s oeuvre over the years might not be surprised to see him in this sort of role. His hair in this film is almost identical to how it looked in the 2008 film Bottle Shock—in which Pine plays an aimless vineyard heir named Bo. Also, does anyone else remember that time then Pine played a reclusive, similarly hirsute rockstar named Eric in Netflix’s Wet Hot American Summer: First Day of Camp? Clearly, this is an archetype he loves to play.

As someone who has long considered Pine her favorite Hollywood Chris, I suspect his experimental fashion choices play no small role in boosting his score. His affinity for pussy bows breaks gender norms, as does his full embrace of short shorts—which remain far more popular in Europe than they are in America, where the mere sight of Milo Ventimiglia’s thighs can leave us all drooling. Also, as someone who has always chafed at formalwear, Pine’s selective recognition of dress codes similarly tickles me.

It will be interesting to see how much of this look lasts once the Poolman hype train is over. Pine copped to the fact that at least some of his red carpet looks have been a form of method dressing. “The film I made is a joyful, silly, playful film, and it just didn’t seem to be the right vibe if I showed up trying to strike Zoolander poses on the carpet,” Pine told the Today show last week, “so I decided to go all-in.” That said, I’m guessing that even if the shorts disappear from his formal wardrobe, the creativity is here to stay. Once a poolman, (hopefully), always a poolman.