The 9 Best Boots to Wear With Skirts, Hands Down

last updated 2 December 2024

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

@sylviemus_ wearing pointed-toe boots with denim skirt and jacket

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:

M&S Collection

Denim Midi Skirt

Nostalgic in the best way.

Toteme

Slim Patent Knee-High Boots

I'm forever grateful for the return of the kitten heel.

YSL

Lee Boots

Super sharp.

PARIS TEXAS

Anja Leather Knee Boot

For a less intense pointed toe, go for these.

River Island

Black Suede Slouch High Heeled Boots

I love the slouchy fit of these.

2. Suede

@ _santinaharrison wearing suede brown boots with a skirt set

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:

ZARA

Striped Knit Pencil Skirt

Yes to the whole set.

Sezane

Anaelle Thigh High Boots

The over-the-knee silhouette looks particularly good with minis.

PARIS TEXAS

Stiletto 60 Suede Mid-Calf Boots

You'll get so much use out of these.

STAUD

Wally Suede Knee Boots

So many influencers own these exact boots.

Anthropologie

Silent D Ivy Knee-High Boots

Such a classic suede boot style.

3. Western

@frannfyne wearing Western boots with skirt and shirt

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:

MANGO

Double Belted Pleated Skirt

The perfect skirt to take you from the office to the weekend.

GANNI

Burgundy Embroidered Western Boots

Ganni's Western boots are pretty iconic.

Matisse

Vegan Acres Tall Western Boots

Such a subtle Western vibe.

PARIS TEXAS

Rosario Embroidered Textured and Croc-Effect Leather Cowboy Boots

Paris Texas has really nailed the modern Western aesthetic.

Anthropologie

Pilcro Mid Western Boots

These would work so well with cream or navy skirts.

4. Biker

@maryljean wearing biker boots with a skirt

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:

& Other Stories

A-Line Mini Skirt

Yes, you can wear your mini even in winter.

H&M

Biker Boots

Just the right amount of buckles.

Jimmy Choo

Biker Ii Boots

Stompy glory.

Reformation

Francesca Moto Boot

These have a really cool vintage vibe.

River Island

High Leg Biker Boots

A great affordable option.

5. Patent

@anoukyve wearing patent boots with suede skirt

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.

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& Other Stories

Suede Midi Skirt

Deliciously good.

ZARA

Patent Effect Heeled Boots

Patent boots don't have to break the bank.

Toteme

Slim Patent Ankle Boots Black

Toteme brings these back every year.

H&M

Knee-High Heeled Boots

Patent leather with an animal effect texture feels both fresh and classic.

GANNI

Black Eyelets Slouchy High Shaft Boots

Note the subtle buckle details—so Nineties.

6. Pop of Colour

@dawn.tan wearing red boots with black skirt

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:

COS

Pleated A-Line Midi Skirt

Such a versatile skirt style.

& Other Stories

Classic Leather Knee Boots

& Other Stories boots always sell out ultra fast.

STAUD

Cami Leather Knee Boots

This glossy red would contrast with black skirts beautifully.

Reformation

Remy Knee Boot

I'm obsessed with this rich burgundy hue.

KHAITE

Ona Suede Knee Boots

Not a fan of the burgundy trend? Embrace khaki instead.

7. Square-Toe

@amaka.hamelijnck wearing square-toed boots with mini skirt

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:

H&M

Pleated Mini Skirt

Time to get the pins out.

MANGO

Leather Boots With Zip

Yes to this colour.

COS

Square-Toe Leather Knee-High Boots

These have an irresistible Scandi vibe.

Vagabond Shoemakers

Blanca Boots

This ankle length will pair well with midi and maxi skirts.

PARIS TEXAS

Roxy Studded Leather Ankle Boots

Ankle boots work really well with longer skirts.

8. Lug-Sole

@annabelrosendahl wearing lug-sole suede boots with a leather skirt

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:

Max Mara

Leisure Scilli Coated Jersey Midi Skirt

A leather-look skirt always looks cool.

Reiss

Ellie Leather Lace-Up Boots

I personally love the combat boot aesthetic.

Russell & Bromley

Tough Line Hi Boots

The dream riding-boot-meets-lug-sole shoe.

Tods

Suede Chelsea Boots

So chic.

& Other Stories

Chunky Chelsea Leather Boots

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:

ZARA

Zw Collection Lace Midi Skirt

The lace really sets this slip apart.

Toteme

Leather Wide Shaft Boots

These are high up on my winter wishlist.

KHAITE

Ona Snake-Print Leather Knee Boots

Snake print is practically a neutral now.

H&M

Slouchy Pointed Boots

Perfect for party season.

Rouje

Doria Boots

If animal print feels too out-there for you, opt for a more subtle croc print.

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Jess Kelham-Hohler is a freelance writer, editor and content strategist. She has been a contributor for Who What Wear UK since 2023. Currently based in London following six years in Washington D.C. and New York, she was previously the Digital Editor for Soho House & Co, an international group of private members’ clubs for creatives. She has interviewed a range of artists, creators and more, including Alighieri founder Rosh Mahtani, photographer Misan Harriman and fashion editor Lindsay Peoples Wagner. Today, she writes primarily about fashion, travel and culture for various publications, and has worked as a copywriter and content strategist for brands such as Belstaff, Olivela and Equinox.