Brad Pitt has hired Timothée Chalamet's stylist. The result is a midlife wardrobe crisis

Telegraph

5 hours ago

If you're a Hollywood actress, the rules around ageing might be punitive and sexist, but at least they're clear. You stay as youthful, slender and sexy as your budget allows, and wear clothes that suggest you can still play the love interest, rather than her mother.
It's different for men. No matter how follicularly challenged or wrinkly, male actors can play the lead until they cark it. As a consequence of this entitlement, many of them age not so much like fine wine as curdled cheese, with little thought given to their grooming or wardrobe. There's even kudos in looking careless and dishevelled: just ask Jack Nicholson.
Today, however, even male actors are required to up their game. Gruelling workouts, surgically enhanced faces and questionable dye jobs are increasingly commonplace, while wardrobes have to be exponentially on point now that men's style is critiqued as assiduously as women's. For those actors deemed to get it right, the spoils are rich. Embracing a more, um, metrosexual style after his James Bond contract ended made Daniel Craig fashion's new darling, with a Loewe ad to boot. Timothée Chalamet 's naturally quirky, expressive style made him fashion's (and the internet's) favourite boyfriend.
Brad Pitt is the antithesis of Chalamet. Where Chalamet, 29, favours sequinned bibs, silver Chanel handbags and pink puffer jackets, Pitt has always been a classic, understated dresser in the all-American mode: part James Dean, part Robert Redford. On formal occasions, his suits were sober, while his off-duty look rarely deviated from some monochromatic combination of grey sweater, white T shirt, Palladium boots and nondescript jeans. Very demure, very mindful, very manly.
But all this has changed. Something is afoot with Pitt's wardrobe; a volte-face so extreme that some are even calling it a midlife crisis. At 61, one would imagine that Pitt was a couple of decades past the phase that might have seen him buy a drum kit, get heavily into wine-making or dye his hair an ill-advised brown in an attempt to revert to the shade of his youth. Besides, he's embraced two of these midlife rites of passage already. But how else to explain his sudden embrace of colour after a lifetime of monochrome, or his enthusiasm for tie-dye, patchwork and crushed velvet?
The explanation is simple: Pitt has enlisted the services of a new, additional stylist, Taylor McNeill (he already works with George Cortina). Nor is it any coincidence that McNeill's most famous client is Chalamet, with whom she's been working since around 2021. While Chalamet has always been an unconventional dresser, McNeill has finessed his style, polishing it in much the same way as Law Roach did with Zendaya. Chalamet's press tour wardrobe for Dune (2021) and A Complete Unknown (2024) made headlines for all the right reasons.
New York-based McNeill, who has worked for Vogue and Vanity Fair, has a particular knack for dressing stars in the kind of outfits and accessories that quickly go viral. As well as styling fashion favourites such as Lorde and Margaret Qualley, it was McNeill who dressed the rapper Kendrick Lamar in Celine boot-cut jeans for his performance at February's Superbowl. Despite their £830 price tag, they sold out immediately, as well as spearheading the current trend for bootcut jeans. Those for whom this achievement remains abstract and therefore underwhelming may like to note that according to Launchmetrics, McNeill's move earned Celine $2.3 million (£1.7 million) in media impact value. In short, putting the right look on the right celebrity at the right time is big business.
Pitt, it seems, is adhering to the same playbook that saw Craig and Chalamet up their profile by upping their eccentricity. At Esquire, it's even referred to as 'Daniel Craig Syndrome', according to the menswear magazine's style director, Johnny Davies. 'Some people may call it a 'midlife crisis', but it's more nuanced than that. As young men, Pitt and Craig were both famous for being very good looking, but they were seldom known as stylish. They're still very good looking, but youth is no longer on their side – Craig is 57, Pitt is 61. One way to keep up the head-turning currency is with clothes.'
For the summer edition of GQ, Pitt was photographed cosplaying a high fashion version of an alpha male, complete with suede Louis Vuitton boiler suit and dirt-smeared £3,350 Saint Laurent leather waders. But this was for a fashion shoot – hardly real life. It was also a form of method dressing that nodded to his starring role in the film, F1: The Movie, in which he plays a racing driver. On the press tour for F1, Pitt mercifully eschewed method dressing in favour of unexpected combinations such as a blue crushed velvet jacket worn with jeans, and a burgundy sweater teamed with tango-orange trousers – an unexpected departure, but it got people talking. Which was the point.
As for whether Pitt's new wardrobe is working, opinion is divided. 'Brad has very conventional good looks. He really suits mainstream fashion – things like leather biker jackets and mid-wash jeans. To suddenly rip up his own rule book and start dressing like Timothée Chalamet, who's half his age, looks a bit tragic. It also looks a bit false, as though he's playing dress-up,' says one British menswear stylist.
Davies thinks Pitt's simply keeping up with the times. 'Today, the trendiest chaps around are not wearing traditional suits – Barry Keoghan, Chalamet and Colman Domingo are bossing the red carpet with experimental and outré looks, and the internet goes mad. Menswear has moved on. The key thing with Craig, and now Pitt, is they actually look like they're enjoying themselves in these clothes. Put it down to not caring what people think after a certain age, put it down to still wanting those IG eyeballs when you're launching a $300 million racing movie – but we're here for it.'