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Since he strapped himself into a pair of suede cowboy boots and low-slung blue jeans on the set of Thelma and Louise, Brad Pitt seized the reins of his epic sartorial ascendency. 

In the simplest of terms, the Hollywood veteran has been around the block when it comes to fashion. From Nineties-era leather jackets and skinny rave shades to asymmetrical skirts sported for blockbuster premieres, the actor’s wardrobe knows no bounds.

Brad Pitt,1988 © Ron Galella, Ltd.
Brad Pitt, 1988

It’s a fine line to tread, being adventurous yet unapologetically cool (without falling into the calamitous category of try-hard) when dressing - especially when the dressee in question is a middle-aged, white man. 

But then again, being Brad Pitt has its perks, one of which being, well, you’re Brad Pitt. Hence, anything goes.

The actor, A-lister and silver screen muse has created a gargantuan web of outfits across the years. It’s hardly surprising, considering his unwavering place of prestige in Hollywood. Yet, unlike some of his fellow famed acquaintances, Brad’s wardrobe has encountered no bumps, no pitfalls, no snags - and we want to know, how?

They say a man is only as good as his tools, and this certainly rings true for Mr Pitt and his Americana closet. It’s filled with innovative brands from Armani to Dior Homme, but then so are the wardrobes of arguably less curiously dressed stars such as Leonardo DiCaprio and Tobey Maguire, for example.

Brad Pitt, 1991© Getty
Brad Pitt, 1991

What helps Brad stand apart from his famed friends, his secret weapon of sorts, is his collection of independent labels. The 60-year-old champions artisan design over luxury tags. 

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MORE: Brad Pitt's girlfriend Ines de Ramon takes major step in relationship as she finalizes divorce from famous ex 

The 2022 Bullet Train press tour consecrated this fact. While promoting David Leitch’s action-comedy, the star stepped out in several headline-hitting looks sourced from smaller fashion businesses. A series of outfits by private-label designer Haans Nicholas Mott, including Brad’s iconic skirt pairing, set the tone for the actor’s idiosyncratic art dealer aesthetic. 

Brad Pitt, 2022© Getty
Brad Pitt, 2022

Odd colours from pale peach to apple green, contrast stitching, slouchy louche tailoring and raw-cut, stringy denim adorned the star’s physique, marking a dramatic shift away from his signature leather jacket, Levi’s and lumberjack shirt ensembles. 

Brad’s 'New Look' and penchant for craft extended to his business affairs. Back in 2019, he soft-launched his very own clothing line God’s True Cashmere alongside friend Sat Hari, a jewellery designer and holistic healer. 

MORE: Inside Brad Pitt and girlfriend Ines de Ramon's stunning multimillion-dollar California home – best photos

MORE: Angelina Jolie's very public romantic history: from Jonny Lee Miller to Brad Pitt

Brad Pitt, 2024© Getty
Brad Pitt, 2024

The brand centres 100 per cent cashmere pieces crafted in Italy, made from yarns sourced from ethical goat farms. Brad’s sartorial DNA is very much evident in the cult brand’s designs, which platform kooky colourways and genderless silhouettes complete with price tags teetering around the £1,500 mark.

So yes, Brad is a sustainable king and certified small brand backer. He’s also unapologetic in his dopamine-inducing style and has yielded the support of fashion sweetheart girlfriends Jennifer Anniston, Gwyneth Paltrow and Angelina Jolie to up his sartorial street cred. 

Brad Pitt and Gwyneth Paltrow, 1996© Getty
Brad Pitt and Gwyneth Paltrow, 1996

Yet all of these factors would be moot if Brad wasn’t the epitome of legendary status in itself. With his glittering, unparalleled career, the allure surrounding his famously avant-garde family dynamic and his effervescent bad-ass yet boyish charm, the actor is nothing short of a cultural icon.

The real reason that Brad has cracked Hollywood’s sartorial code? Because he’s Brad Pitt, that’s why.