Any trouser-phobe will tell you that skirts aren't only for summer; they open up a world of styling opportunities come winter, too. All you need are the perfect boots to pair with them.
This season, however, it seems there are more boot options to choose from than ever before—pointed-toe, patent, biker, Western, to name but a few—which in turn makes deciphering which styles look best with which outfits all the more difficult. So shifting our focus back to the aforementioned skirt, we decided to uncover the best boots to wear with skirts, with a little help from some of our fashion friends.
Keep scrolling to see nine flawless boot-and-skirt pairings. Then, proceed to shop everything you need to re-create the look for yourself.
See the Best Boots to Wear With Skirts This Winter, According to a Fashion Editor:
1. Pointed-Toe
Style Notes: Sleek, sexy and undeniably cool, pointed-toe boots are back with a vengeance. While you can lean into their sensuality by styling knee-high styles with mini skirts or slinky dresses, you can also follow Sylvie's example and use them to elevate an otherwise casual skirt, like a denim version.
Shop the Look:
Nostalgic in the best way.
I'm forever grateful for the return of the kitten heel.
Super sharp.
For a less intense pointed toe, go for these.
I love the slouchy fit of these.
2. Suede
Style Notes: Sure, suede boots may not be the most practical style for British autumn and winter—but that's what suede protector spray is for! These styles are certainly super elevated, and look so chic when paired with knitted skirts.
Shop the Look:
Yes to the whole set.
The over-the-knee silhouette looks particularly good with minis.
You'll get so much use out of these.
So many influencers own these exact boots.
Such a classic suede boot style.
3. Western
Style Notes: Yes, the cowboy boot is back. Avoid looking like you're going for a costume by investing in ultra-chic versions with subtle Western details, whether that's Southern-style embroidery or a cool buckle detail.
Shop the Look:
The perfect skirt to take you from the office to the weekend.
Ganni's Western boots are pretty iconic.
Such a subtle Western vibe.
Paris Texas has really nailed the modern Western aesthetic.
These would work so well with cream or navy skirts.
4. Biker
Style Notes: Subtly different to the current Western style, Biker boots are a little more robust, chunky and lean heavily into the metalwork. Use these to toughen up a more delicate skirt like a mini black skirt or a silky slip.
Shop the Look:
Yes, you can wear your mini even in winter.
Just the right amount of buckles.
Stompy glory.
These have a really cool vintage vibe.
A great affordable option.
5. Patent
Style Notes: My Instagram scrolling has taught me that the best winter looks are all about mixing textures, and Anouk's outfit is a perfect example of this in action. Patent boots come in really handy for this, complementing suedes, knitted textures and wool brilliantly.
Shop the Look:
Deliciously good.
Patent boots don't have to break the bank.
Toteme brings these back every year.
Patent leather with an animal effect texture feels both fresh and classic.
Note the subtle buckle details—so Nineties.
6. Pop of Colour
Style Notes: If, like me, your winter wardrobe mainly consists of dark tones, boots are a great way to inject a jolt of colour. This season, burgundy boots are the way to go.
Shop the Look:
Such a versatile skirt style.
Other Stories boots always sell out ultra fast.
This glossy red would contrast with black skirts beautifully.
I'm obsessed with this rich burgundy hue.
Not a fan of the burgundy trend? Embrace khaki instead.
7. Square-Toe
Style Notes: Pointed-toe may be dominating the boot conversation, but square-toe styles are still holding their own. Personally, I love how they act a slightly tougher edge to skirt-based outfits.
Shop the Look:
Time to get the pins out.
Yes to this colour.
These have an irresistible Scandi vibe.
This ankle length will pair well with midi and maxi skirts.
Ankle boots work really well with longer skirts.
8. Lug-Sole
Style Notes: Ever since The Row dropped their lug-sole ankle boots, the trend has really taken off. Thankfully, now there are plenty of other options to choose from, too.
Shop the Look:
A leather-look skirt always looks cool.
I personally love the combat boot aesthetic.
The dream riding-boot-meets-lug-sole shoe.
So chic.
Wear with minis or maxis.
9. Animal-Print Boots
Style Notes: Whether it be leopard, snakeskin or croc, animal-print has seen a major boost in popularity amongst the fashion set. The easiest way to incorporate this bold trend into you winter outfits? Opt for a boot of course!
Shop the Look:
The lace really sets this slip apart.
These are high up on my winter wishlist.
Snake print is practically a neutral now.
Perfect for party season.
If animal print feels too out-there for you, opt for a more subtle croc print.
-
Suddenly, All The Row-Style Girls Are Breaking This Fashion RuleAnd you should, too.
-
I Want to Build a New Wardrobe—30 Incredibly Elegant Pieces I'm Eyeing From theReplica Store Winter SaleBring on the chic outfits.
-
I Forgot About These Winter Boots Until Meghan Markle Styled a Pair In the Most 2025 WayGood thing they're on sale.
-
I'm a Professional Shopper—These Are the 3 Best Categories From theReplica Store Winter SaleThese chic pieces are selling out fast.
-
These 30 Incredibly Chic Picks From theReplica Store Winter Sale Scream Cool GirlTime to up your fashion game.
-
We're Fashion Editors—Everything We Saw, Wore, Did, and Ate During NYFWLet's dive in.
-
Brace Yourself: 2025's Most Divisive Shoe Trend Has ArrivedYou'll either love it or hate it.
-
I Know You're Stylish If You Tuck Your Jeans Into Boots Like These 5 Chic WomenDon't be scared.
