They're such a staple that you probably don’t think about how to style ankle boots, pulling on your favourite pair with the same old baggy jeans/cargo pants/leggings – delete as appropriate – without a second thought. And while this is what good, no, great, shoes are surely made of, the ankle boot deserves more, especially as it’s going to keep serving you, not just until the stirring of spring but far after.
Especially, it has to be said, if you follow our guide to how to style ankle boots in 2026, which isn’t anything revolutionary, sure, but does involve thinking outside the ‘trench and jeans’ box. A new-season twist on this tried-and-tested formula might be a leather moto jacket, perhaps in burgundy or burnt orange even, with straight-legged denim or an oversized trench with a pleated miniskirt.
Keep scrolling to see – and shop – the six pairings we’ll be rotating over the next few months, with ankle boots that run the gamut from the snake-printed to the impressively stack-heeled.
Leather Jacket And Jeans
A pointed black ankle boot with a modest heel is an off-duty model signature for obvious reasons (it’s both practical and polished). That doesn’t mean you can’t have fun with the styling. Try a leather moto jacket, which feels slightly more directional than a biker or bomber.
Belstaff Mollison Jacket
Aligne High-Rise Straight-Leg Jeans
Toteme Leather City Boots
Jigsaw Mini Heckfield Suede Tote
Brown Coat And White Jeans
Snake print, however subtle like this streamlined boot from Aeyde, needs paring down. Team brown outerwear with a duo of white, such as a crisp button-down and ecru denim.
& Other Stories Shawl-Collar Wool Maxi Coat
With Nothing Underneath The Boyfriend Exaggerated Cuff
Frame Le Slim Palazzo
Aeyde Sofie Leather Ankle Boots
Casual Separates And A Pop Of Colour
Lili Curia’s playful lace-up boot – with its flash of yellow and buckle ankle strap – can firstly be grounded with utility beige separates. Then simply introduce a colourful base layer as your finishing touch.
Carhartt WIP W' Kelly Shirt Jacket
Polo Ralph Lauren Slim-Fit Cotton Tee
Carhartt WIP W' Brady Pant
Lili Curia Kitt Lace-Up Boot
Trench Coat And Miniskirt
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A trench coat, cable-knit and miniskirt is a failsafe trio that needs an equally traditional boot, in this case a cowboy style by Russell & Bromley. For evening, add a flourish in the form of lace or otherwise statement hosiery.
Massimo Dutti Cotton-Blend Trench Coat
Brora Aran Jumper
COS Pleated Wool-Blend Skirt
Russell & Bromley Calle Boots
Flight Jacket And Balloon-Leg Trousers
A flight jacket’s cool sensibility is offset with a big-personality boot. Seek out a square-toed style, or something patent and stack heeled, to add punch to a plaid shirt.
Sacai Pleated Padded Shell Bomber Jacket
YMC PJ Overshirt
Arket Barrel-Leg Corduroy Trousers
Miista Cass Boots
Cropped Jacket And An A-line skirt
A ‘shoe boot’ isn’t the easiest style to wear, unless you lead with a bare calf plus a skirt that’s a) high-waisted and b) gently A-line. Add a cropped leather jacket – in eye-catching brick or teal – and aviator sunglasses.
Nanushka Cropped Okobor™ Alt-Leather Puffer Jacket
Massimo Dutti Pleated midi skirt with appliqué
Arket Glossy Leather Ankle Boots
Burberry Classic Pilot Sunglasses
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