20 of the best ankle boots to see you through autumn and winter

Curating your colder weather wardrobe means considering a timeless autumn coat and cosy knitwear (we can’t get enough of the cardigan trend this year), but it also means carefully choosing our winter footwear.  

We say ‘winter footwear’, but considering the UK’s climate, you’ll probably end up wearing them on those chilly spring days too. So, when you consider cost-per-wear, it’s certainly worth the investment. And September and October is the prime time to snap up a new pair of boots, as both high street stores and designers alike bring out the very best of their autumn/ winter collections. 

This year, winter boots are chunkier than ever. In fact, searches for chunky boots have soared by 1550 per cent, according to LIKEtoKNOW.it. Other big boot trends taking stores by storm are square toes, rain boot-style rubber footwear and the croc-effect leather look is still here to stay.

These are some of our favourite styles to shop before they sell out… 

Squared Toe Leather Ankle Boots, £89.99, Mango

Black Leather-Look Flared Block Heel Boots, £32.99, New Look


Square Toe Suede Chelsea Boots, £380, Paris Texas

Athena Leather Ankle Boots, £295, L. K. Bennett

Croc Leather Heeled Ankle Boots, £135, & Other Stories

Leather Ankle Boots With Raised Detail On The Heel, £150, Uterqüe

Leather Western Block Heel Ankle Boots, £69, Marks & Spencer

Quilted Ankle Boots, £69, Charles & Keith


Peyton Leather Ankle Boots, £119, John Lewis & Partners


Chunky Recycled Rubber Chelsea Boots, £195, Ganni

Velo Snakeskin Heeled Boots, £79, Urban Outfitters

Brando Croc-Effect Leather Ankle Boots, £360, Staud

Nanette Leather Platform Ankle Boots, £295, Grenson

High Profile Chelsea Boots, £29.99, H&M

Flat Sock Ankle Boots With Zip, £49.99, Zara

The Brogued Chelsea Suede Ankle Boot, £200, Fairfax & Favour


Mid Heel Leather Ankle Boots, £190, Arket


Bertine Logo-Print Square Toe Leather Boots, £460, Acne Studios

1460 Crazy Horse 8-Eye Boots, £149, Dr. Martens


Aquarius Burgundy Chunky Leather Boots, £109, Topshop