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
(Image credit: Future)
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
(Image credit: Future)
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
(Image credit: Future)
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
(Image credit: Future)
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.
Shop the Look:
HUSH
Meridah Italian Wool Coat
HUSH’s new line of winter coats looks so expensive! This Italian wool piece is a classic.
COS
Cashmere Funnel-Neck Jumper
There’s a reason everyone loves COS’ cashmere. Its super soft and a fraction of the price of designer versions.
lululemon
Align™ High-Rise Pant
I’ve been testing these leggings for a few weeks and can tell you that they are elite.
The Garrett boot is back in stock! Thank you, Sézane. The block heel gives that bit of oomph, but is still very walkable.
5. Oversized Shirt + Knee Boots
(Image credit: Future)
Style Notes: Ok, truth be told, the Glenn Martens x H&M capsule has pretty much sold out entirely. But fear not, you can still get the look. Our junior fashion editor, Imani, got a first look at this capsule and is still obsessed to this day. Copy her vibe with an oversized pin-stripe shirt, worn like a dress, plus a pair of knee-high sculptural boots to stomp around in. It’s a look which is edgy, eye-catching, and a little bit punk, if you ask me.
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A shirt dress is such a versatile piece. Tie a knit around your waist for a cosy twist.
AZALEA WANG
Stiletto Heel Studded Knee Boots
The folded details and snap closures give these boots a sculptural shape, perfect for adding character to an otherwise simple look.
ACNE STUDIOS
Small Shearling-Trimmed Leather Shoulder Bag
ACNE STUDIOS’ camera bags are having such a moment.
Spinelli Kilcollin
Sterling Silver Acacia Ring
Add a dainty sparkle to your look with this classic ring from Spinelli Kilcollin.
6. Long Sleeve Tee + Sweats + Knee Boots
(Image credit: Future)
Style Notes: I didn’t see this one coming, but yet, it totally works. Pairing heeled, pointed black boots with baggy sweat pants, plus a ’90s combo of a long-sleeved t-shirt and plaid shirt tied around the waist, is actually kind of chic! For the days when you can’t decide between your cosy favourites and luxury pieces, wear both for a look that says, “I woke up like this.” A burgundy handbag and classic Ray-Ban Wayfarers give this look extra sartorial brownie points.
Shop the Look:
Free People
We the Free Perfect Oversized Long Sleeve Top
Free People’s basics are too good to miss. This oversized tee comes in a whole range of colours and sizes.
M&S
Pure Cotton Checked Shirt
I spotted Monikh wearing this shirt lately, showing just how easy it is to chuck on.
ARNE
Women’s Relaxed Straight Leg Jogger
Cloud soft and perfect light grey tone. These joggers are just the ticket for tucking in to your boots for that grunge-y look.
Charles & Keith
Pointed-Toe Stiletto-Heel Knee-High Boots
The whole Who What Wear UK office is obsessed with Charles & Keith. These boots prove why.
7. Knitwear + Midi Skirt + Knee Boots
(Image credit: Future)
Style Notes: Trust Marilyn NK to get the knee-boots brief on point. She partners her luxury, skin-tight high-shine boots with the viral COS skirt, in this season’s favourite purple hue. To keep cosy, she sticks to a staple black crew knit cashmere sweater, and finishes things with a Margaux bag from The Row and statement aviator sunnies from Phoebe Philo. This is the perfect H-to-T look for cosy, pub lunches with family or a wine date with friends. The boots take centre stage due to their glossy, luxe sheen.
Shop the Look:
Rise & Fall
Black Cashmere Midweight Crewneck Jumper
ZARA
Checked Midi Skirt With Belt
PARIS TEXAS
Jane Leather Knee Boots
ZARA
Limited Edition Leather Tote Bag
Shop More Knee Boots:
COS
Leather Knee-High Boots
ZARA
Split Suede Knee-High Boots
schuh
Damari Leather Pull On Boots
Whistles
Black Knee High Riding Boot
Free People
We the Free Rapids Riding Boots
BOTTEGA VENETA
James Intrecciato-Trimmed Leather Knee Boots
ZARA
Block Heel Knee-High Boots
Free People
Frye Campus 14l Wide Calf Boots
Reiss
Leather Knee-High Block-Heel Boots in Black
Vagabond Shoemakers
Meryl Tall in Brown
Reiss
Block-Heel Knee-High Boots in Chocolate
ZARA
Embroidered Leather Cowboy Knee-High Boots
KHAITE
Colt Glossed-Leather Knee Boots
H&M
Heeled Knee-High Boots
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