The Slouchy ‘Pirate’ Boots That Defined The 2000’s Are Back

There are certain fashion memories that immediately transport you back. For some, it’s a whiff of Juicy Couture velour; for others, it’s the sight of a perfectly oversized Chloe Paddington bag. But for anyone who lived through the style heyday of the early 2000s, it’s the slouchy boot - pirate-inspired, slightly undone, and forever etched into the memory of fashion’s most photographed women.

Of course, we can’t talk about this silhouette without nodding to Vivienne Westwood, who first introduced her now iconic Pirate Boots in the early ’80s, complete with exaggerated buckles. Over time, the look softened, buckles disappeared, the shape slimmed down but the spirit of rebellion stuck. Today, you’ll still spot revamped versions on Westwood’s own site, while beat-up, well-loved pairs circulate on secondhand platforms.

Kate Moss made them her calling card in 2003, often pairing her Vivienne Westwood slouchy suede pair with micro-minis and bohemian scarves, her tousled hair the ultimate finishing touch. Sienna Miller followed closely, cementing the boot as part of the boho-uniform that dominated the decade. And long before the Y2K wave, Princess Diana herself had a fondness for the silhouette, stepping out in a sleek black pair that lent her daytime looks a dose of tame glamour.

Back then, the styling formula was straightforward: throw them on with anything, skinny jeans, army jacketor blazer, and the boots did the rest. They had that magic balance of rugged and polished - suggesting you’d rolled out of bed, but in a way that still managed to make the front page of mag.

Fast forward to now, and slouchy boots are firmly back in the zeitgeist. At Copenhagen Fashion Week, countless showgoers leaned into the silhouette, pairing them with sharp tailoring or minimalist co-ord’s to prove just how versatile they’ve become. The runways followed suit: Louis Vuitton’s Autumn/Winter collection reimagined the slouchy boot in shiny leather, while Balmain offered sculptural versions that nodded to their 2000s ancestors but with a distinctly modern bite.

The result? A surge in demand and a fresh wave of styles ready to shop. From designer knee high iterations to relaxed suede options that feel lifted straight from a paparazzi shot circa 2004, there’s never been a better moment to revisit the trend. So, why not trade these trainers for boots this autumn?

Shop: Slouchy Boots

Renee Washington, Grazia's digital fashion and beauty writer, lives online. With a penchant for wispy lashes and streetwear, she writes about the worlds of fashion and beauty from the viewpoint of the modern fashion girlie..

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