8 foolproof ways to wear ankle boots

The humble ankle boots has remained a timeless staple in our wardrobes, even when sleek knee-highs and buckled biker boots dominated the trend cycle of late. In fact, the classic silhouette, which, for many of us, marked our first foray into heels as teenagers, should be considered a year-round staple.

Like many other revivals we’re witnessing at the moment, the ankle boots of winter 2025 aren’t far removed from the styles we wore in the Noughties. Slouchy, suede buccaneer boots, Kate Moss for Topshop-inspired snakeskin and second-skin styles are cropping up once again.

Ankle boots come into their own as the weather gets cooler, but unlike taller styles, they aren’t suffocatingly hot, making them the perfect transitional piece. They’re also versatile when it comes to styling, as ankle boots tend to slip neatly under, or layer over, most trouser or jeans silhouettes. Plus, they also look great when styled with socks and tights on the chilliest days, too.

Key styling references come courtesy of the autumn/winter 2025 runways. At Louis Vuitton, pointed, heeled and shearling-lined ankle boots were paired with everything from tartan dresses to cargo trousers, jumpsuits and rain macs – most of which were styled with woollen knee-high socks for added winter appeal. Isabel Marant’s supple leather ankle boots, meanwhile, came studded and ruched around the ankle, styled with lace fishnet tights, black leathers, plaid and pinstripe.

Louis Vuitton AW25.

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Isabel Marant AW25.

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Missoni offered an especially nostalgic take with flat, pointed buckle boots in snakeskin, suede and leather. Styled with shorter hemlines, they were balanced by oversized outerwear, slouchy knitwear and striped scarves. At the other end of the spectrum was Cecilie Bahnsen’s collaboration with The North Face, which yielded storm-faring interpretations: zippered ankle boots with Gore-Tex soles and signature floral accents, perfectly offset with knee-high socks and girlish, flouncy skirts.

Cecilie Bahnsen AW25.

Stefania Danese

Missoni AW25.

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“When an item remains in your wardrobe rotation for over a decade you know that it’s worthy of a place in the fashion hall of fame. For me, it’s a pair of Topshop snake-print ankle boots that I splurged on (relative to my minimum-wage salary) in my early 20s,” says Joy Montgomery, Vogue’s shopping editor. “With a low block heel and pointed toe, they’re the perfect style to wear with straight-leg jeans, plus the pop of print is an easy way to add interest to basics. The snake-print boot has been central to Khaite’s autumn/winter collections in recent years, plus I’ve spotted some chic pre-loved Celine styles on eBay. But this season I’ll still be sticking with my old faithfuls.”

So whether you’re going for something minimalist, boho or sharp and tailored, there’s an ankle boot to suit every occasion. From thick-soled stomper boots that add grit to slip skirts to sleek pointed-toe pairs that sharpen denim and cargo trousers, the possibilities are endless. Scroll to find out how to style this season’s best ankle boots now.