When we talk about style icons, we often think of those people who have always stayed true to one aesthetic, embracing a look and, with only a few tweaks over time, turned it into a trend worth following.
But we know there’s always the exception to the rule, and that exception is called Brad Pitt.
Boyish face, blue eyes, and ash blonde hair. The shirtless kid with the hairdryer in Thelma & Louise is now 61 and never misses a chance to surprise us with elegant, bold, modern, casual, and refined looks—making change his favorite accessory.
A sex symbol from the start
After years of small roles and cameos, Pitt’s breakthrough came in 1993 when audiences fell in love with the story of two best friends: Thelma Yvonne Dickinson and Louise Elizabeth Sawyer. But that wasn’t all. It only took 7 minutes on screen as the thief J.D. for Pitt to be crowned by the global press as a sex symbol. That image of him on a motel bed, shirtless and wearing a cowboy hat, is burned into the memory of thousands—just like that final shot of the blue Ford Thunderbird flying off.
Taking the easy route—relying on blue eyes and blonde hair—would have been too simple, or maybe just too boring.
So maybe to shake off that label, we start seeing his hair growing longer, shirts getting more oversized. The look changes, but the charm remains.
Between film and reality: dressing multiple personas
Throughout his long career as an actor and producer, several films have clearly shaped his off-screen style too. At a time when personal stylists were not yet common, the transformation from a white t-shirt and jeans boy to a gritty bad boy was influenced heavily by working with the same costume designer on three different films in just 10 years.
Michael Kaplan is the name behind Pitt’s looks in Seven, Fight Club, and Mr. & Mrs. Smith.
So, while detective David Mills hunts down the madman John Doe (Kevin Spacey), Brad Pitt adopts his character’s haircut and adds some messiness, keeps the mustache and goatee, and even brings the white shirt and casual jacket combo to red carpets.
A couple of years later, around 1999, Pitt—perfectly embodying Tyler Durden, Edward Norton’s alter ego in Fight Club—seems to channel multiple personalities and enjoys dressing them all.
In the pages of W Magazine, he seems to still embrace his character’s aesthetic—down to wearing the same motorcycle tee from the film. Printed shirts and the ever-present fur coat make a comeback too.
A style full of twists
His red carpet looks from that era were completely different: clean lines, neutral colors, wide collars, and structured jackets. Rounding out his public appearances at the time was Jennifer Aniston, with her iconic haircut copied by girls all over America. Together, they were the poster couple of relaxed, casual fashion with simple silhouettes that quickly became a ’90s and early 2000s style reference.
We all remember the black outfits from the 1999 Fight Club premiere and the 2000 Oscars.
This simplicity continued off-stage too. In countless paparazzi shots, the Pitt-Aniston duo always sported basic pieces like cargo pants and plain t-shirts. The only creative touches were accessories like sunglasses and hats—from classic visors to beanies and boonie hats.
But Mr. Pitt is always ready for the next plot twist. In 1999, it came in the form of a Rolling Stone photoshoot.
To break away from everything previously mentioned, he pitched photographer Mark Seliger a bold idea: a photoshoot in women’s clothing. Today, we wouldn’t blink—but in 1999, seeing a man in feminine outfits wasn’t exactly common. The result? One of the most iconic editorials ever. If republished today, we’d probably hang up that photo of Pitt in a pink sequin mini-dress again.
Another turning point: Brangelina
In 2005, yet another plot twist: the breakup with Jennifer Aniston and—by early 2006—the announcement of Angelina Jolie‘s pregnancy.
The playful, casual style that had defined him until then, as seen in a 2004 Vanity Fair photoshoot by Nick Knight, took a new direction, and Pitt’s image shifted to something more polished and elegant.
Suits and tuxedos, complete with bow ties, became red carpet staples—though Angelina often stole the spotlight. Even in daily life, his looks seemed more refined, and shirts were a constant. His hair also grew longer again, but unlike the decade before, he now appeared consistently well-groomed—so much so that Chanel chose him as the face of Chanel N°5. It’s as if his style was saying that the sex symbol had evolved into a socially and professionally committed father.
Once again, the line between his roles and reality seems very thin, and the aesthetic we see in films like Mr. & Mrs. Smith, the Ocean’s trilogy, The Curious Case of Benjamin Button, and The Tree of Life is also present off-screen.
The Rediscovered ’90s
They say women get a haircut after a breakup, while Brad Pitt seems to go for a total style overhaul. In May 2017 (a little less than a year after his separation from Angelina), GQ published an editorial titled Brad Pitt Talks Divorce, Quitting Drinking, and Becoming a Better Man, and Ryan McGinley’s photos instantly bring us back to the Brad from nearly twenty years earlier.
Back come the printed shirts, oversized fits, and more casual pieces like sweaters and tank tops.
New Decade, New Look
The keyword of recent years is: color.
Like the yellow suit by Umit Benan B+ he wore in a 2022 GQ feature. Or the green linen suit – paired with adidas x Gucci Gazelles – worn at the Bullet Train premiere in 2022. Or the lavender one recently chosen for the Mexican premiere of F1 (out June 25). And then, the blue velvet jacket by Willy Chavarria seen as he exited a New York hotel just days ago.
Of course, many are wondering whether – like in the ’90s – there’s a costume designer or collaborator behind this new look. Well, just like his style, his habits have evolved: many of his recent outfits are curated by stylist Taylor McNeill, who also works with Kendrick Lamar and Timothée Chalamet.
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A Constantly Changing Style Icon
It’s impossible to pick a favorite version of him: from classic and elegant to playful and edgy, from “dad mode” to ’90s sex symbol. But every time we see him, we want to own at least one piece he’s wearing – just to see how a multicolor tie-dye tracksuit would look on us.
If there’s one thing Brad Pitt has taught us, it’s that we should never get used to his looks – we can only admire their beauty and originality, and look forward to the next surprise from his wardrobe.
Herb Ritts
