7 Chic and Practical Ways To Wear Knee-High Boots for Winter 2025

It’s that time of year when flip-flops, ballet flats, and sandals are pushed to the far back of our minds, and we reach for closed-toe, warm, and weather-proof shoes and boots (the clouds are rumbling as I write this). Ankle boots and mid-calf styles are perfect for the transitional months of autumn, especially in suede, but there is one style of boot that is both practical and stylish for the colder days ahead: leather knee-high boots. These are not only trending now but are also a versatile staple in your capsule wardrobe, pairing beautifully with everything from skirts of all lengths, dresses, sweatpants (yes, you heard that right!), leggings, and even trusty jeans.

I've been wearing a reliable pair of knee-high boots from high-street favourites Whistles for several weeks now, and they have become my go-to for everyday looks. Sitting just below my knees, with an almond toe and flat, rubber lug soles, they are crafted from premium black leather. Their shape and material make them suitable for all weather conditions, and they easily elevate casual evening outfits, too. I'm not the only one adopting this trend. Through my social media scrolls and walks around London, I've seen other style-conscious people styling out knee-high boots as well. Not only in flat styles, I’ve observed an increase in patent, lace-up, heeled, buckled, pointed-toe, sculptural, and form-fitting knee-high boots, demonstrating just how adaptable this trend can be and how well it suits many personal aesthetics.

If you're eager to put your best foot forward this winter, keep reading for seven tips on how to style knee-high boots. Plus, I'm sharing my favourite pairs ready to shop now.

1. Funnel-Neck Jacket + Lace Skirt + Knee Boots

Style Notes: Just because its suddenly chilly and drizzly, doesn't mean you can't dress up. Make like Hannah Lewis, and don a funnel-neck jacket (buttoned to the top), a pretty, lace-trimmed skirt and high-shine high-knee boots with a heel for a look that serves chic city-slicker. This is a masterclass in how to wear heeled knee-high boots in a dressier, day-to-night fashion. The monochromatic palette keeps this look timeless, and will take you from desk-side meetings to dinner plans in one fell swoop.

Shop the Look:

Róhe

Reinvented Leather Jacket

Róhe is the jacket brand to know now.

Reformation

Carolina Silk Skirt

Such a pretty skirt, which also comes in 9 other colours!

ZARA

Fitted High-Heel Boots

Let these boots do the talking. So chic and a little bit sexy.

KHAITE

Kye Snake-Effect Leather Shoulder Bag

Add an exotic touch to your look with this snake-effect bag from KHAITE.

2. Suede Jacket + Blue Jeans + Knee Boots

Style Notes: I've been spotting fashion-people bringing back the Y2K trend of tucking their jeans into their boots, and I'm kind of into it! A little bit country, a little bit nostalgic, it's a look which is great for weekends in the city and, yes, the countryside. Go for a pair of straight-let jeans (so much easier to tuck in), and a boot with a bit of give. A skin-tight or glove-style boot isn't your friend here, so go for something with a bit of room to manoeuvre, with a chunky sole. A suede or barn jacket is an apt way to finish the look and keep you cosy. Mini sunglasses and a sparkly bag give this ensemble a Kate Moss at Glasto vibe.

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The kind of jacket you will revisit for years to come. I love the leather collar and chocolate hue.

AGOLDE

'90s Pinch High-Rise Straight-Leg Jeans

If you want a '90s looking jeans, go for AGOLDE.

TOMMY HILFIGER

Leather Knee High Biker Boots

These boots mean business, and the moto details give them an edge.

RABANNE

Chainmail Shoulder Bag

Rabanne's bags will add infinite shine to your look.

3. Matching Set + Sunglasses + Knee Boots

Style Notes: For something a little more show-stopping, look to a lace-up boot, preferably with a fierce pointed toe. The laces will give a little extra kick of visual interest and give the illusion of a longer leg. Follow in the footsteps of Lily Russo-Bah, and go all-out with the rest of your ensemble. A pink nylon funnel-neck jacket and matching skirt give this a sci-fi spin. The paparazzi are sure to be chasing your tail in this look, so the addition of oversized sunglasses will keep their camera flashes at bay.

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For the full 'fit, grab the skirt too. So cute!

ALAÏA EYEWEAR

Mask D-Frame Acetate Sunglasses

ALAÏA's eyewear line is so iconic. The Mask style is there signature shape.

The lace detail and perspex heels mean these boots will make heads turn.

4. Long Wool Coat + Leggings + Knee Boots

Style Notes: If dressing like a moody, cloudy day is your thing, take note now. Team a slate grey chunky knit (a roll-neck if you're super chilly), plaid shirt and simple leggings with your trusty knee boots, just like Ingrid Edvinsen, for a monochromatic, yet cosy fit, which is spot on for weekend-ing. A structured wool coat, a black leather bag and sleek oval sunnies top it all off, stopping the look from looking too untidy. This outfit is ideal for off-duty days, perhaps doing groceries, picking up local treats from the farmer's market or catching up at the coffee shop with friends.