Autumn has well and truly arrived. There are nature’s signals, including fallen leaves, a chill in the air and a “chance of rain” forecast for the weeks ahead – and, in some parts of the UK, a dramatic alphabetical series of storms. But there are also this season’s customary style signals, like layers, outerwear and warm-weather accessories.
The clocks have changed, and so too has our focus on what to wear for the cooler (and inclement) months ahead. Now marks the obligatory unearthing of your favourite winter boots – or hunt to find a suitable new pair – which can be put to good use right up until spring (and beyond). As for how to wear them now? During the autumn and winter months, pairing boots with jeans has long been a favoured combination among the fashion set, endorsed by off-duty supermodels and street-style crowds alike.
Beloved for its simple appeal, a boot-and-jeans partnership is inherently versatile, whether worn for a weekend stroll (obligatory latte in hand) or daily commute. It isn’t a groundbreaking statement to wear an ankle boot or knee-high with jeans – nor something that could command serious attention – but there’s a reason why so many women have championed the formula for decades.
Carolyn Bessette-Kennedy gave boots and jeans her own minimalist spin in the ’90s, often reaching for bootcut jeans and polished black boots that felt both understated and elegant. Kate Moss, meanwhile, made both staples trusted cornerstones of her off-duty wardrobe, pairing slouchy boots with slim-fit denim in the early 2000s. And while closer-cut jeans were trending styles of bygone eras, more recently, fashion month attendees have gravitated towards baggy silhouettes, worn with heeled, pointed-toe boots peeping out from hemlines.
Read more: The Key Autumn/Winter 2026 Trends To Know Now
A great boot can make for a great outfit, requiring little more than jeans that fit well. Shop ’s edit of the best boots to wear with jeans, below.
Biker boots
Animal-print boots
The Depths of Time Beaded Silver-Plated Agate Necklace
Riding boots
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Slouchy boots
Faux Fur Trim Flight Bomber Jacket
Sock boots
A.Emery