Boots To Wear With Dresses And Skirts

Boots To Wear With Dresses And Skirts

If you love dresses and skirts, then you’ll love this roundup of the best boots to pair with them. From knee-highs to ankle boots, there’s a style in here for everyone.

There are so many ways to wear boots with dresses or skirts. If you’re not sure where to start, we’ve got some awesome ideas for you. Whether you’re looking for something casual or something more dressy, we’ve got options that will fit your style and budget!

Casual Boots To Wear With Dresses And Skirts

  1. Chelsea Boots: These Chelsea-style boots are perfect for pairing with jeans or leggings as well as dresses and skirts. They have a matte black finish with a chunky heel that makes them super comfortable for all day wear. The elastic sides make it easy to slip these on over your pants!

Boots To Wear With Dresses And Skirts

8 Boots That Should Be Worn With Skirts to Be Fully Appreciated

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—hiker, thigh-high, combat, lace-up, 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 onto 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.


Style Notes: While leather boot styles work just as well with skirts, there’s no denying that the softer finish of suede loans itself to floatier skirting. Monikh’s knitted midi looks the retro part with her tan numbers.

Shop the skirt:

Self-Portrait Knitted Midi Skirt (£220)

Shop the boots:

Sosandar Blake Taupe Suede Zip Knee High Boot (£149)

Saint Laurent Mica 75 Brown Suede Ankle Boots (£700)

Boden Scallop Detail Knee High Boots (£230)


Style Notes: Slouchy, knee-high boots look excellent with just about every skirt length, but they look their best with a miniskirt, as evidenced by Ada. Add sheer tights if you prefer more coverage.

Shop the skirt:

Mango Check Miniskirt (£30)

Shop the boots:

Paris Texas Croc-Effect Leather Knee-High Boots (£460)

& Other Stories Squared Knee High Leather Boots (£205)

River Island Grey RI Studio Leather Slouch Boots (£120)


Style Notes: Key details, such as lace-up fronts, are too pretty to be covered up by long trousers. Instead, pair them with a split-front or wrap skirt like Katherine to show them off to great avail.

Shop the skirt:

& Other Stories Faux Wrap Midi Skirt (£95)

Shop the boots:

Manu Atelier Duck Colour-Block Leather Ankle Boots (£261)

LK Bennett Arabella Ankle Boots (£329)

Whistles Dahlia Lace-Up Heel Boot (£199)


Style Notes: Much like suede, white and ecru tones offer a softer boot alternative to that of the often-favoured black-leather styles. We love how Marissa wears her white ankle boots with black opaque tights.

Shop the skirt:

Hollister Cord Mini Skirt (£35)

Shop the boots:

Zara Leather Boots (£149)

NastyGal Block Heel High Ankle Boots (£33)

Charles & Keith Chalk Stitch-Trim Ankle Boots (£69)


Style Notes: Combat boots are a wonted staple, and lately fashion types have been wearing the grunge footwear with their more summery pieces to pull them into the right season. Case in point: Tamara’s slip skirt and chunky boot pairing.

Shop the skirt:

Ganni Ruched Lavender Satin Skirt (£110)

Shop the boots:

AllSaints Donita Leather Boots (£229)

Malone Souliers Bryce Leather Combat Boots (£595)

Kurt Geiger Vegan Tread Lace Up (£149)


Style Notes: For some skirts, structured boots can look too chunky. In this instance, turn your attention to sock-style boots that fit tightly around the ankle to create a streamlined leg silhouette. Case in point: Ellie’s neoprene pair.

Shop the skirt:

Rixo Kelly Leopard Skirt (£185)

Shop the boots:

Dune Optical Stretch Sock Ankle Boots (£125)

Office Anagram Square Toe Sock Boots (£92)

& Other Stories Heeled Leather Sock Boots (£135)


Style Notes: Western boots look cool with just about anything you throw at them, though mini skirts, much like Imani’s, offer an unexpected and modern alternative to prairie dresses and blue denim.

Shop the skirt:

Monki Pleated Mini Skirt (£15)

Shop the boots:

Isabel Marant Denvee 50 Black Leather Knee-High Boots (£655)

Jigsaw Woods Leather Western Boot | White (£200)

AND/OR Santino Suede Knee High Western Boots (£169)


Style Notes: It would be remiss not to mention 2021’s It boot, the chunky track-sole. Although they look great with everything, from jeans to dresses, we think skirts balance out their cumbersome proportions perfectly—as does Sya.

Shop the skirt:

Massimo Dutti Asymmetric Mini Skirt With Patch Pockets (£70)

Shop the boots:

COS Chunky Boots (£180)

Gianvito Rossi Chester Leather Ankle Boots (£785)

& Other Stories Chunky Sole Leather Chelsea Boots (£165)

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