How to wear pirate boots in 2025 Style tips and everything you need to know about Vivienne Westwood and Kate Moss's favorite shoes
There’s always a moment, between the end of summer and the beginning of fall, when you feel the need for something new. Something that breaks the routine of the usual mid-season pieces and brings a bit of flair back to the wardrobe. This year, that turning point has a clear name: pirate boots. Impossible to ignore, they’ve taken over runways, social media feeds, and the windows of top fashion brands, reasserting themselves as one of the key pieces for fall-winter 2025. With their deconstructed shape, soft folds, decorative buckles, and an aesthetic that swings between rebellion and romance, they emerge as one of the most versatile footwear styles of the season. In a landscape where microtrends come and go at lightning speed, pirate boots stand out with a defined personality and a rare quality: they integrate naturally into everyday outfits, without ever going unnoticed. But how do you actually wear them? How do you style them without looking like Jack Sparrow, and what still makes them so iconic decades after their debut? In this guide, through historical references, current trends, new icons, and practical advice, we’ll break it all down.
Vivienne Westwood, Kate Moss, and the origins of the style
You can’t talk about pirate boots without mentioning Vivienne Westwood, who debuted a model in 1981 that would become a cult fashion item. The collection, called Pirate, marked a shift from the harsh punk of previous years to something more theatrical and ornate, yet equally radical. The boots were tall, soft, full of unexpected details, and exuded romantic outlaw vibes. The original model, with its rounded toe, multiple buckles, and worn leather, became a cultural reference before it was even a fashion item.
In the 2000s, Kate Moss brought them back, making them a boho chic wardrobe essential. She wore them effortlessly, paired with mini dresses, fur, sunglasses, and tousled hair, making every outfit feel spontaneous. One iconic photo shows her sunbathing on a Ford Explorer in a Los Angeles parking lot, the door wide open as if she'd just hijacked it. It's 2001, and that image, seemingly stolen from a cult film, still has the power to evoke an era. I'm not the only one wondering what Kate was feeling in that photograph. The Haim sisters recently recreated the scene for their new album promo, with Danielle wearing the same pair of Westwood pirate boots that defined not only that Californian afternoon, but the aesthetic of an entire decade.
Piratecore takes over the runways and the fashion crowd
The return of pirate-style boots isn’t just a visual revival, it’s part of a broader aesthetic shift called piratecore. Positioned between romanticism and rebellion, this fashion trend reinterprets the past for a hyper-connected, image-saturated present. The inspiration stems from cinematic and literary narratives but is reinterpreted with modern materials and functional details, creating a product that manages to be theatrical without ever becoming caricatural. It's no coincidence that brands like Balmain, Zimmermann, Ralph Lauren, and even Onitsuka Tiger have embraced this direction in their FW25 collections. The offerings range from voluminous, structured designs with hidden pockets built into the shaft, like those seen at Balmain, to lighter, almost poetic versions, as showcased by Zimmermann and Ralph Lauren, where the leather gently drapes around the leg, maintaining a casual yet elegant look. Dolce & Gabbana, on the other hand, took a stand with models that carry a strong rock edge, full of personality, while Miu Miu reinterpreted the concept through a more feminine and urban lens, with sleeker lines and vintage-inspired details. The result? In every variation, while preserving their original spirit, pirate boots adapt to more contemporary vibes, making them a perfect match even for more minimalist looks. That’s why a new generation of style icons loves them. In addition to the Haim sisters, pirate boots have become a signature piece for figures like Iris Law, known for her edgy, experimental approach, and Bella Hadid, recently photographed wearing a pair of Alexander McQueen boots from the Spring/Summer 2003 collection. She paired them with a sleeveless, high-neck cream top, a beige suede mini skirt, and a chocolate-brown jacket. A calibrated, confident look that proves even a piece with strong character can find balance in a modern wardrobe. Pirate boots today don’t shout rebellion, they whisper it, in style.
How to wear them (for real) in 2025
One of the most frequently asked questions is exactly this: how do you wear pirate boots without looking out of place? The good news is that, despite their bold appearance, they are surprisingly versatile. This type of footwear allows for the creation of layered, elaborate outfits, but also cleaner, more minimalist pairings, while still maintaining a visually striking element. Worn with skinny jeans or pants tucked into the boots, these styles bring dignity back to the boot tuck trend, which had seemed relegated to the archives of the 2010s. The effect is instantly edgier and more put-together, without feeling forced. With long floral-print dresses or flowing fabrics, pirate boots add character and break up the romantic feel, giving the look a more grounded tone. Pairing them with midi skirts and oversized mohair sweaters is also effective, playing on the contrast between soft volumes and strong structure. In an urban key, the most successful combo includes a mini skirt, oversized blazer, and a crossbody bag. A few well-balanced elements are enough to make the look feel contemporary and dynamic.
Details to watch: shapes, materials, colors
In 2025, the most sought-after models are those that balance personality with wearability. The lines have softened, with wide shafts, intentionally imperfect stitching, and rich textures that echo the world of craftsmanship. Soft leather, brushed suede, and vintage-treated leather are among the most common materials, but there are also versions in technical fabrics or with shearling details, perfect for deep winter. The focus is on flexible construction, able to adapt to the wearer’s body and step. As for colors, the palette remains earthy and versatile: black, brown, light tan, but also burgundy, olive green, and midnight blue. Buckles are often more decorative than functional, adding movement to the overall look. In some cases, the soles are lighter and more flexible than the boot’s bulky appearance might suggest, making them ideal for all-day wear. These are small, but essential, details that transform a historical piece of footwear into a genuinely desirable item.
The trend that (maybe) will stick around
Not every trend is destined to last, but the pirate boots of 2025 seem to offer something more. Perhaps because they don’t just ride the Y2K revival wave, but fit into a broader conversation, one of expressiveness, functionality, and subtle theatrical touches. They’re a piece that tells a story and lends itself to personal interpretation, without being forced. Those who’ve already rediscovered them wear them naturally, integrating them into urban, minimalist, or boho outfits without feeling out of place. And that’s often the sign that a trend has evolved from a passing fad into a truly desirable item. In an era that demands authenticity, these boots respond with character, without ever taking themselves too seriously.
