There are few things the layperson has in common with Kate Moss. Supermodel status may elude us, but the feeling of a long, hard day followed by a weary lean against a car is universal – as the icon demonstrated on the streets of Los Angeles in 2001.
Sporting a long-sleeved Breton top, a white mini skirt and Vivienne Westwood pirate boots, Ms Moss lapped up the California sunshine in a highly meme-able moment playfully recreated by many, including girlband Haim for the release of their 2025 single ‘Everybody's Trying to Figure Me Out.'
Kate’s knack for delivering an iconic paparazzi moment never faltered – nor did her love affair with pirate-inspired boots. Throughout the Noughties, the model rehashed her beloved boots - a high fashion silhouette that has received a high street makeover in recent weeks.
© RedfernsFirst introduced in Vivienne Westwood’s autumn/winter 1981 Pirate collection, the designer’s eponymous boots were a punkish take on historical dress, with turn-down leather cuffs, buckled straps and a swashbuckling silhouette.
© GC Images
© GC ImagesCreated alongside Malcolm McLaren, the footwear helped define Westwood’s early New Romantic aesthetic, drawing on the romanticism of highwaymen, dandies and buccaneers.
Recent seasons have witnessed a subtle reemergence of pirate boots on the runway, with buckled leather and lace-up options championed by Marques’Almeida and Ann Demeulemeester, plus shearling-capped knee-highs courtesy of Chloé.
© Imaxtree
© Imaxtree
© ImaxtreeThe high street was quick to take note, with household names from Schuh to M&S democratising the designer shoe for all to enjoy.
Whether styled with a striped look à la Kate, tucked beneath a billowing boho dress or paired with bootcut jeans for a dose of Y2K nostalgia, pirate boots offer a welcome departure from the predictable. Consider them the season’s most unlikely sartorial treasure.
Shop our favourites below.
Pirate boots to shop this season:
Pirate Boot
Vivienne Westwood
Vivienne Westwood’s iconic Pirate boots return in supple black leather, complete with slouchy cuffs, chunky buckled straps and silver-tone hardware. First introduced in 1981, this rebellious design remains a sartorial icon.
Dorsten Suede Pirate
Schuh
Featuring a vintage-inspired tan colourway with an autumnal suede finish, Schuh's buckled beauties are an affordable take on the playful trend.
Suede Buckle Strap Mid Calf Flat Boots
M&S
Marks & Spencer’s khaki suede boots offer a high-street take on the pirate aesthetic, with mid-calf styling, buckle detailing and a practical flat sole.
Janina Boots
Miista
Tap into captain-chic with Miista’s black leather Janina boots, which serve up statement buckled detailing with a square toe and sculptural heel for elegant after-dark wear.
Buckled Biker Boots
Bershka
With chunky soles and buckle-heavy straps, Bershka’s tan-toned biker boots look ready to ride straight out of a Kate Moss street-style archive.
Cade Boots
ASOS Design
Available in rich chocolate brown and timeless black, ASOS' heeled boots are set to inject your everyday style with a heavily-buckled touch of sass.
HELLO!'s selection is editorial and independently chosen – we only feature items our editors love and approve of. HELLO! may collect a share of sales or other compensation from the links on this page. To find out more visit our FAQ page.
