Back from the 2000s — the iconic Kate Moss boots everyone wants

Fashion loves to come back around. This time, it has unearthed one of the most striking pairs of shoes from the 2000s: "pirate" boots, once made iconic by Vivienne Westwood and Kate Moss. Two decades ago, they were worn with short dresses, voluminous coats, and a carefree ease that created the "I woke up like this" effect.

Read why the legendary "pirate" boots are back in style this fall, according to British Vogue.

Pirate boots make a stylish return for Fall 2025

The first "pirate" boots appeared in 1981 in Vivienne Westwood's Pirate collection. They were an attempt to escape punk and find a new language — one that was freer and more artistic, with a hint of defiance. With soft leather, folds, and several straps instead of zippers, every detail hinted that imperfection could be beautiful.

Then Kate Moss came along and made them legendary. The photo of her standing next to an old Ford in Los Angeles, wearing a mini dress and these boots, became a symbol of an entire era. There was something completely authentic about them — not glossy, not staged.

Today, history is repeating itself. A new generation of fashionistas, including Bella Hadid, the Haim sisters, and TikTok influencers, are digging out old pairs from vintage boutiques and bringing them back into fashion. "Pirate" boots appeared on the catwalks of 2025 at Balmain, Zimmermann, Ralph Lauren, and Dolce & Gabbana. Some designers added theatricality, while others made them more minimalist, yet still rebellious.

How to style trending boots now?

Wear them with skinny jeans, a flowing dress, a short skirt, or an oversized jacket. Contrast works well here: chunky shoes with light fabrics, or a restrained top with a little chaos at the bottom.

For winter, look for models made of thicker leather or with a sheepskin lining. They have a textured look and will keep your feet warm. 

Read more:

The best short boots for Fall 2025 — comfortable and chic

How to choose the best winter sneakers for comfort and style