8 Foolproof Ways To Wear Ankle Boots This Autumn

I'll always remember my first pair of “grown-up shoes”: a pair of silver, block-heeled Topshop ankle boots, bought in a size three on sale for less than £20. At the time, they felt like a big deal, with their clippy-cloppy heels and sock-like slim-fit leather. I wore them on repeat for much of my teens until I entered my all-black era and flogged them on Depop in favour of a pair of stompy Dr Martens. For many of us, the classic ankle boot marked our first foray into heels as teenagers, and while sleek knee-highs and buckled biker boots have dominated the trend cycle of late, the low-profile style will always remain a wardrobe staple.

Like so many other revivals we’ve witnessed over the past few seasons – low-rise jeans, leggings, velour tracksuits and studded belts among them – the ankle boots of autumn/winter 2026 aren’t a million miles away from the styles we wore back in the Noughties. Slouchy suede buccaneer boots, robust lace-ups, Kate Moss for Topshop-inspired snakeskin and second-skin styles are all cropping up again, bringing with them a welcome dose of nostalgia.

The key styling references for how to wear ankle boots now come courtesy of the autumn/winter 2026 runways. Louis Vuitton reignited interest in the silhouette last year with shearling-lined styles, and continued its exploration of the ankle boot with leather cut-out versions this season. Isabel Marant approached things from a similarly boho school of thought, showing suede wedge-heeled boots alongside slouchy leather and zebra-print styles, worn with rolled-down socks, glossy leathers, straight-leg jeans and shrugged-off faux fur.

Elsewhere, Victoria Beckham made a case for a more streamlined approach, pairing skinny trousers with flat-soled, square-toed Chelsea boots. But for those who prefer something with a little more heft, Miu Miu’s chunky lace-up styles brought a hiking sensibility to the mix, which were offset with sweet bow-adorned woollen minidresses.

Cowboy boots, meanwhile, have lost none of their appeal. Dior Men and Gabriela Hearst both offered ankle-height Western styles, with a less overtly rodeo-inspired alternative to the knee-high versions that have dominated in recent seasons. Missoni offered perhaps the most nostalgic proposition of all – flat, low-profile, pointed-toe boots with buckle detailing, rendered in crocodile-effect finishes, suede and leather. Styled with heavy tweeds and the house’s signature chevron stripes, they were the sort of boots Kate Moss might once have worn with skinny jeans and a slouchy knit while pounding the pavements of St John’s Wood in the 2000s.

“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 the 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.”

From thick-soled stompers 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.

With baggy jeans