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Why Is Brad Pitt’s Style Aging in Reverse?

Brad Pitt isn’t aging backwards. He is allowing his wrinkles to carve character into his face in the tradition of Robert Redford. Yet in an ironic twist on one of Pitt’s defining films, The Curious Case of Benjamin Button based on F. Scott Fitzgerald’s short story of the same name, Pitt’s fashion does indeed seem to be aging backwards. Over the past year, the 59-year-old actor has been busting an exuberant — and highly textural, occasionally gender-neutral — wardrobe. He looks fuzzy like a stuffed animal at times. It’s not so much that he’s trying to look younger, it is more like the confidence of age has unleashed a sense of fun we haven’t seen before. And yep, it looks great on him.

So why can Pitt get away with this playful game of dress-up? First of all, as Derek Zoolander would say, he’s “really, really good looking.” It is also his swagger: it is like he is daring anyone to tell him he can’t dress like a slap-happy Smurf. That kind of chill can’t be bottled. Men are generally allowed to age more whimsically than women: think the whole Dad oeuvre of goofy hats and T-shirts. If women dress eccentrically, on the other hand, they are immediately labelled a kook. It takes a lot of DGAF to surmount that. 

Pitt is onto something very important here, something we can all learn from. There is really no reason we, too, can’t unleash how we feel inside on the outside. The confidence it takes to pull off Pitt’s playful period is the key. What else is aging good for, if you can’t shrug off worry about other people’s opinions and express yourself?

Pitt launched his new look on the summer 2022 European promotional tour for Bullet Train, busting out baggy linen suits in Creamsicle, cotton-candy pink and bright green. He wore a skirt suit, also in linen, this time brown with an asymmetrical rough hem by an artisanal brand named Anecho. When Variety asked him what was up, he offered an apocalyptic explanation: “I don’t know. We’re all going to die, so let’s mess it up.” 

Then early this year, filming Wolves in Manhattan, there emerged the new fuzzy theme. There was a smattering of “what in the middle life crisis is this” on Twitter when he was snapped in February in head-to-toe fleece. Turned out it was a costume for the film, but then the internet went deep into the ‘Pitt’ of its recent photo vaults and found lots more examples of the heartthrob wearing cushy clothes. In particular, one white fuzzy bucket hat he seems to be enamored with. But if you look closely, it is what he wears in his off-duty, on-the-way-to-set outfits, that says much more.

If you look back over time, Pitt has been a fashion shape-shifter throughout the phases and high-profile romances of his life. He often seems to morph into the woman he’s dating. He was blond when he was with patrician Gwyneth Paltrow. He took on a surfer/hippie vibe when he was married to America’s Sweetheart, Jennifer Aniston. And he worked the bad boy look in motorcycle leathers in the early years of marriage to Angelina Jolie, as she emerged from her own Goth era and before she made her own transition to the humanitarian queen of expensive and tasteful neutrals. It must be noted, he is now said to be dating a much younger woman, health coach Ines de Ramon, 30. A possible catalyst for a revamped look?

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Pitt has also tried on every form of facial hair: a carousel of retro Pitt photos looks like a chiselled Mr. Potato Head playing with limitless moustaches and beard iterations. None of them, repeat none of them look bad on him.

Yet, he remains instantly recognizable, whether it be in his shaved head period of the mid 2000s, or as cowboy Brad, an image burned into public consciousness in his breakthrough role as the boy toy in Thelma & Louise. There is also classic movie star Pitt, as frozen in the Oceans 11 franchise, a rake in a tux. Quentin Tarantino told GQ (in a fashion-forward cover story last summer, featuring Pitt in Ziggy Stardust-style face makeup and silver Tom Ford) that he considers Pitt “one of the last remaining big screen movie stars.”

He’s going for an artier look these days and indeed it sounds like art is more important to the noted collector as of late. He’s always been an ardent architecture fan, and is a sculptor himself. While his producing game at Plan B has put out a string of literary films, he has also built a recording studio on his South of France winery, Chateau Miraval, and launched an organic skincare line, Le Domaine, formulated with natural molecules from leftover grapes. He also just launched a playful clothing line called God’s True Cashmere. 

Pitt has also weathered a bunch of storms. His divorce and periods of separation from his kids has been a very public agony. He has also been vocal about his decision to go sober. He settled a messy US$20.5 million lawsuit around his Hurricane Katrina house building charity last year. There is more angst surrounding Jolie’s sale of her half of their marital chateau. Celebrities have problems, just like us. But he’s embracing the good stuff with gusto, and his humanity is showing through his fashion sense.

So what can we learn from Brad’s closet adventures? Well, if you’ve spent your life lamenting you don’t look like Brad Pitt, there’s good news! Brad Pitt doesn’t look like Brad Pitt anymore, either! Wish your husband would shake things up a bit after a 20-year style rut? The trick here is to start with accessories and work your way into more colour and texture a little at a time. You don’t have to go all the way to nail polish and skirts and fuzzy hats. A bold pair of sneakers is a foolproof way to dip your toe in the more eclectic style game. A gaily striped sweater is a layer you can take off if you begin to feel uncomfortable. Pop on a golf-style bucket hat in a bright colour for weekend chores. Try the velour, velvet or the towelling hoodie, you will be surprised how much sensory luxury texture can add to your day. Let loose, you’ve earned it, just like Brad.

Always asking questions,

—Leanne Delap