Of all the A-list Hollywood actors, Brad Pitt, who fronts British GQ’s July 2022 cover, is the one who has truly proved that style has no age limit. Just look at his wardrobe of late: as the frontman of Tarantino’s Once Upon A Time… In Hollywood, he’s inspired us all to rock Hawaiian shirts, denim jackets and cowboy boots (even if we don’t have a 1960s Cadillac coupé to go with them). Meanwhile he’s been serving a grunge game (plaid shirts and ripped jeans) as good as that of the late Kurt Cobain.

But Brad Pitt started gaining points in the style game long ago, primarily in the 1990s – that oh-so retro, oh-so iconic era during which he rose to fame on screen. So we’ve hopped back to that all-important decade (with a couple of his late-1980s ‘fits thrown in for good measure) and compiled 10 of his sharpest style lessons. We’ll take any excuse for a fashion throwback, especially when it looks as good as this…
1. You need a double-breasted suit…
When: 1991
Why: We’ll say this time and time again: you need a DB suit. If there’s one throwback to prove that, it’s Brad Pitt in 1991. Opting for a boxy, louche fit and wide notch lapels (top points), his finishing accessory was a floral printed tie.
2. …And a (long) leather coat
When: 1997
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Why: Sure, we love a good old battered motorcycle jacket as much as the next guy, but Brad Pitt’s making the case for another layer of leather here: a long, single-breasted overcoat. A bit more formal but with a dose of insouciance (see that slightly unbuttoned shirt for proof), this was some serious Matrix styling (before The Matrix even happened).
3. Layer your white essentials
When: 1998
Why: The most basic item in any man’s wardrobe? A white T-shirt. But winter is on its way, the temperatures are dropping and our go-to essential suddenly isn’t the most practical item to wear. The key to keeping warm? Layer it over a white vest like Brad Pitt, then top it with a jumper and denim jacket.
4. Subtle double denim is the way forward
When: 1991
Why: We’ll forever stan double denim, but for a subtle take on the statement, follow in the footsteps of Brad Pitt and layer it up with some simpler pieces. White T-shirt beneath, boxy brown blazer on top, suede Western boots and some circular shades will do the trick. Top points for casual coolness.
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5. Suede is the ingredient for easy elegance
When: 1993
Why: We could talk about Brad Pitt’s longer locks for hours here (how the hell does he pull off every grooming move?), but we’ll focus on that suede styling instead. Completing a long-sleeved white shirt and grey pleated trousers, his brown suede waistcoat seals this outfit of minimal tailoring with a little nod to Western wear. The result? A big howdy to easy elegance.
6. Micro shades for the win
Year: 1999
Why: Name a more iconic 1990s shade – Brad Pitt will wait. The release of The Matrix in 1999 caused quite the hype, in part because of Keanu Reeves’ iconic role, in part because of his extremely cool wardrobe. Those micro shades became the item of the year, and thanks to guys like Brad Pitt who pulled them off with force, the revival item of the decade. Style them with a slick black suit and shirt (collar pulled out) for maximum effect.
7. The open collar still looks sharp
When: 1997
Why: How to show a knowledge of formalwear without looking like you’re trying too hard? Opt for a slim grey suit and pastel yellow shirt à la Brad Pitt in 1997. Make sure to unbutton that shirt and pull the collar out over the lapels of your blazer for a real nod to the 1990s. Big style energy, sure, but it still catches the right kind of attention today. Especially when the grounding boots are leather.
8. The humble vest is in
When: 1988
Why: You might not have the guns to rival Brad Pitt, but that’s no reason as to why you shouldn’t wear a vest. Whether you go peak-Pitt or replicate how vests were worn under suits in Tom Ford and Giorgio Armani’s Spring/Summer 2021 collections, the vest is in.
9. The bigger the ‘fit, the better
When: 1988
Why: Sure, today Justin Bieber is championing the big, baggy ‘fit, but before him Brad Pitt was doing it best. Case in point: this look consisting of an oversized worn-in leather bomber jacket and loose-fitting cotton slacks, which have been drawn in with a belt at the waist for an optimum balloon-esque aesthetic.
10. Invest in a power tie
When: 1992
Why: No, Pitt didn’t have a career on Wall Street before taking on household name status – this is what he wore to the 1992 7th Annual IFP/West Independent Spirit Awards. Wearing an impressive double-breasted suit consisting of a baggy, undone jacket and high-waisted trousers, it was the finishing touch of a power tie akin to those worn by George Clooney and Patrick Bateman in American Psycho that secured his ‘fit a place on this list.
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