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Saturday, October 17, 2026

The ultimate winter boot guide: From the slouch to the wedge and the pixie, this is how to wear every new style

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After the scorching summer we’ve endured, I’m fully embracing boot season. There’s nothing better than slipping on cosy socks, closed-toe shoes and not having to think about your pedicure. From slouchy boho stompers to wedges and the new Pixie boot, these are the trending autumn boot tribes to join. Start walking!

The slouch

Squashy, rather than stiff boots are all the rage again – though at luxury boho brands Chloé and Zimmermann this silhouette is a stalwart on the runway each season. The brave will wear theirs with bare legs, à la the crowds at Copenhagen Fashion Week, but they also work nicely with sheer or black tights, and look fabulous with floaty midi dresses or A-line skirts. Top tip: to balance your outfit proportions the top of the boot should be hidden by the hemline.

The new pixie

AKA the flattest boot we’ve seen in decades. If you’re opposed to heels, the new short Pixie is for you. The sleek, low-profile silhouette and flat stacked heel pair immaculately with slightly cropped straight-leg cigarette trousers or jeans. Don’t even think about tucking in a pair of skinny jeans or, worse, leggings. We don’t want you resembling Peter Pan.

The fold over

I know what you’re thinking: didn’t Puss in Boots wear these? While the cartoon cat forgot to wear trousers, the thigh-skimming cuffed boots were right on the money. The kids have declared fold overs are in – one colleague’s Gen Z daughter has bought three pairs in the past few months. Kurt Geiger’s cuffed Chiltern comes in wine, dark brown and black and is a current bestseller. Marella’s knee-high glossy statement style is known among shoppers as a ‘party’ boot because the solid heel is ideal for dancing. Wear yours for just that! Frocks and skirts are your dressing solution here. Leave your wide-brimmed hat at home.

The wedge

These sculptural shoes forgo a traditional heel for a wedge that stretches from sole to floor along the length of the foot. From Alexander McQueen to Isabel Marant, fashion’s biggest design houses are selling them as a means of gaining extra inches of height comfortably. If you’re seeking conversation-starting footwear, look no further than Arket’s sleek snake-print pair. Or try the subtle Oxford demi-wedge from John Lewis, which is much more wearable. This is a goes-with-everything boot. The styling possibilities are endless.

The riding 

Sturdy and equine inspired, these classic tall boots are a shoo-in. Fairfax & Favor has found the perfect balance of practicality and style with its tan investment Kimberley style – Zara Tindall and the Olympic dressage rider Charlotte Dujardin are big fans of this heritage brand. Or head to DuoBoots where you can select your custom calf fit. When getting dressed, consult Claudia Winkleman’s Traitors look – she’s spot on pairing hers with plain black leggings. Otherwise, tuck into your straight-leg jeans or wear over sheer black or brown tights. Giddy up.

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