The Tucked Knee High Boot Trend is Taking Over in Winter 2025

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As soon as the temperature drops and the frosty weather settles in, one footwear style jumps straight to the front of my winter rotation: boots. Timeless and practical, knee-high styles in particular have been dominating the conversation for several seasons now, well and truly cementing their place as a capsule-wardrobe hero. And, always on the hunt to spice up my cold-weather outfits, there’s one easy styling hack that’s making a comeback, and it’s tucking your knee-high-boots into your jeans.

(Image credit: Getty Images)

You might be thinking this trick isn’t particularly new, and you’d be right! When I first spotted it bubbling on my Instagram feed, I was vividly reminded of a noughties Kate Moss, striding through London in heeled pirate boots, which she had tucked her skinny jeans into. Divisive then, and perhaps even more divisive now. Or, if I look even further back to the ‘80s, when a Princess Diana was often spotted stalking grassy polo pitches in straight-leg jeans and a loose blazer, complete with knee-high boots on full show. Yet, there’s something about the way the styling trick is being utilised today which feels undeniably refreshing.

Fashion person Isa Sung wears the tucked knee high boot trend. She wears dark wash boot cut jeans, black boots and a knitted cardigan. This image was recently taken from her Instagram.

Part of the hack’s appeal lies in its universality. Regardless of age, aesthetic or winter wardrobe pieces, knee-high boots and jeans tend to feature, and are ready to become and so this styling hack feels like an easy win. And the fashion set is proving that every silhouette works. Are you a low-rise, slouchy jeans person? The subtle scrunch adds a laid-back polish for just the right amount of interest. Or are bootcut jeans your go-tos this winter? The one-in-one-out look casts a powerful visual, adding a modern appeal which feels oh-so 2025.

Fashion person Marylin wears the tucked knee high boot trend. She wears a pinstriped blazer, blue jeans and a black knee high boot. This image was taken from her Instagram recently.

And as if it couldn’t get better, this trend is technically free, costing no more than your favourite pair of jeans and knee-high boots. With both “thick denim jeans” and “leather knee-high boots” trending on Google, the resurgence of this styling trick couldn’t come at a better time.

Fashion person Lou Northcote wears a tucked knee high boots trend. She wears a yellow jacket, blue jeans and brown leather knee high boots.

So, if you’re ready to try the styling hack worth its weight in denim, scroll to discover my edit of the best knee-high boots and jeans ready for tucking this winter.