Wondering What Boots to Wear With Skirts? We've Decoded 8 Specific Styles That Work Best

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 eight 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 Autumn, According to a Fashion Editor:

1. Pointed-Toe

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

(Image credit: @sylviemus_ )

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.

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2. Suede

@ _santinaharrison wearing suede brown boots with a skirt set

(Image credit: @_santinaharrison)

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.

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3. Western

@frannfyne wearing Western boots with skirt and shirt

(Image credit: @frannfyne)

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.

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4. Biker

@maryljean wearing biker boots with a skirt

(Image credit: @maryljean)

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.

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5. Patent

@anoukyve wearing patent boots with suede skirt

(Image credit: @anoukyve)

Style Notes: My Instagram scrolling has taught me that the best autumn 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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6. Pop of Colour

@dawn.tan wearing red boots with black skirt

(Image credit: @dawn.tan)

Style Notes: If, like me, your autumn 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.

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7. Square-Toe

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

(Image credit: @amaka.hamelijnck)

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.

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8. Lug-Sole

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

(Image credit: @annabelrosendahl)

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.

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Freelance Fashion Editor

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.