For the longest time, I only had eyes for block-heel ankle boots; no other boot style got a look in. However, a few years ago, I invested in the first knee-high boots I’d had since my teens, and they were a game changer. Aside from jeans, I very rarely wear trousers. Nine times out of 10, you’ll catch me wearing a midi dress. And after years of enduring chilly calves and not-quite-right hemlines and boot heights, knee boots swooped in and made every outfit (read: dress) I wore so much chicer and more put-together.
Now, I currently own four pairs of knee-high boots: an on-trend chunky pair from M&S, which I bought as soon as I saw them on a colleague; a beige suede option from Sézane, which I invested in hoping it would make my clothes feel a little more French; a basic black pair that I pull on whenever I’m in a rush; and a burgundy set, which I snapped up last year in an attempt to bestow my winter wares with a bit of colour. They’ve all enjoyed a handful of wears already this year, and I know they’ll make me feel at my most stylish, even in the depths of winter.
As for outfits with knee-high boots, there’s no shortage of inspiration out there. Like me, influencers seem to be wearing little else on their feet right now, so I’ve rounded up all of my favourite looks in one place for you to peruse (and shop) at your leisure. From skirts to denim, scroll on to see outfits with knee-high boots I rate.
Outfits With Knee-High Boots We're Seeing Everywhere:
1. Knitted Midi Dress + Matching Bag
Style Notes: Knitted dresses can err on feeling casual, but adding a pair of knee boots—especially shiny, patent ones—instantly elevates them for more glossy occasions.
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This looks seriously cosy.
These boots will definitely earn you lots of compliments.
This isn't quite a shoulder bag but the colour match with the boots is perfection!
2. Slip Skirt + Suede Jacket
Style Notes: I first bookmarked this chic outfit from Monikh Dale a while ago, but it still holds up for 2024. While slip skirts might feel summery, there’s no need to pack them away when you have a pair of knee boots and some suede outerwear at your disposal.
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This timeless jacket will work with jeans, dresses and of course, a slip skirt. PS, keep your eyes peeled for the restock. This is just too good.
This fluid midi skirt will work hard in your wardrobe.
This deep brown pair is the ultimate finishing touch to this 70's inspired fit.
3. Trench Coat + Mini Skirt
Style Notes: I’m petite, and one of my favourite tricks for making me look that little bit taller is wearing heeled knee-high boots with a shorter hem to make legs look longer.
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Grab this in a size up for that oversized fit.
You can also wear this mini with a cream cable knit, patterned tights and chunky boots.
A pair to love for a lifetime.
4. MINI SKIRT + SHORT JACKET
Style Notes: You don't have to pack away your mini skirts once winter comes around. A pleated mini will look just as chic with knee-high Chelsea boots and your favourite short jacket. Simply add a chunky knit and some thick tights.
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This lighter grey shade is super versatile.
Simply add tights.
These are at the top of my winter wishlist.
Throw in everything and go!
5. Black Maxi Dress + Leather Trench
Style Notes: Nothing feels more seasonally appropriate than a ribbed dress and leather. Being a dress sort of person, I plan on re-creating this outfit ASAP.
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This dress could easily work for day or night.
A leather trench will always come in handy.
I cannot express enough how happy I am flat boots are trending this year. And this pair are pure perfection.
6. Striped Knit + Leather Mini
Style Notes: A striped knit is a great investment, and I love how Jessica has styled her oversized version with a mini skirt and flat suede boots. Just add tights and thermals underneath to make this outfit cold weather-proof.
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A timeless knit.
This ultra-cool skirt is also available in petite sizes.
The contrast of the suede and leather is what really makes this look.
7. Sharp Suiting + Simple Silhouette
Style Notes: Tucking your jeans into boots is one thing, but a pair of suit trousers? This member of the street style set has convinced me to give this suited look a whirl.
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Grey is definitely the colour of the season and this suit is an easy way to give it a go.
Wear with a classic shirt, or layer knitwear on top for a more relaxed take on tailoring.
I've been dreaming about these boots for a long, long time.
8. Denim Dress + Cream Knit
Style Notes: Chiara has convinced me that I need a denim dress to pair with my tan knee-high boots. I love how she's added a cosy cream knit on top to make this look cold-weather appropriate. Delightful!
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A denim dress is so versatile to wear across all seasons with a switch of an accessory.
Fold the hem under to show off the denim dress.
Tan boots are a great option for autumn and beyond. Add them to all your floral dresses for an easy, stylish look.
9. Chunky Knit + Midi Skirt
Style Notes: You can't beat a cable knit jumper. Fact. And I love how Frann has layered hers over a casual check shirt and midi skirt. This look is also proof brown is the new black this season.
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This style looks so cosy.
Hello to my new favourite skirt.
So pretty.
These are such a sleek shape.
10. Classic Jeans + Black Leather
Style Notes: Classic vintage-wash denim and edgy black leather is my favourite outfit combination. Throw in a pair of knee-high boots in an expensive-looking mock-croc finish, and this is a look I’d gladly wear on repeat during the colder months. Thanks for the inspo, Linda Tol.
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This leather looks as soft as butter.
Arket always has the exact pair of jeans I'm after.
This brand makes seriously good boots.
11. Denim Jacket + Jeans
Style Notes: Marilyn's cool outfit is perfect for the transitional season. Opt for knee-high sock boots tucked under oversized denim for a modern twist on the Canadian Tuxedo.
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Continue wearing denim jackets in the winter.
A modern silhouette.
You can easily slip these under jeans.
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Trust Me: I've Looked—These Are the Chicest Knee-High Boots on the High StreetFrom kitten to stiletto.
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The Ballet Is One of the Most Elegant Places You Can Go—6 Outfits That Match the Classy VibeTime to get fancy.
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7 Easy “Jeans and a Nice Top” Outfits Elegant Dressers Are Wearing on Repeat Right NowHow to get ready in ten minutes or less.
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Gwyneth Paltrow Wore the Chic Boot Trend That Goes Best With Slim-Leg TrousersI'm digging out my slim-fit trousers for this.
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I Can't Face Wearing Heels—5 Flat-Boot Looks That Are Just As PolishedThe chunkier, the better.
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Sienna Miller’s Boots Could Be Called "Dated", But Her Jeans Are So 2025An outfit she wore whilst hanging out with J.Law!
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Hold the Jeans—Celebrities Have Confirmed They're Be Wearing Leggings and Boots All Winter LongI'll be doing the same.
