8 Easy Dress-and-Boot Combos That Work Every Single Time

There are so many dress trends to get excited about this season. From preppy minis to sequin-adorned maxis, the S/S 24 runways were fruitful in the frock department. And the same can be said for the high street's offering. Just one look at the new-in sections, and you'll see the resurgence of slinky slip dresses on the one hand and an array of oversized knitted silhouettes on the other, so it’s safe to say just about every style and taste has been catered for.

Of course, you'll need to right footwear to pair with your new dresses. And since it's still cold outside, boots are the obvious choice. I don't know about you, but from October until at least early April, my boot collection takes pride of place in my shoe-drobe and all the pumps, sandals and trainers get shoved to the back. So it's lucky that boots + a dress = a match made in heaven.

It's difficult to go wrong with this combination, but certain pairings are particularly chic. Scroll on to see our favourite examples of wearing dresses and boots while we wait for spring to arrive.

1. Neutral Knitted Dress + White Boots


(Image credit: @vikilefevre)

Style Notes: Instead of defaulting to dark tones at this time of year, step out in top-to-toe neutrals like Anne-Victoire did. White boots feel fresh and go so well with beige, sand and off-white shades.

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2. Silk Slip Dress + Tall Boots


(Image credit: @deborabrosa)

Style Notes: Hands up if you struggle to style slip dresses in February. I'm with you, and I've found that the addition of knee-high boots balances things out beautifully. Just layer a blazer on top to beat the chill.

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3. Red Dress + Biker Boots


(Image credit: @mcristinastyling)

Style Notes: This punchy combination feels very 2024. Opt for a red knitted dress now, then swap it for a lighter-weight iteration come spring.

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4. Floral Midi Dress + Patent Knee-High Boots


(Image credit: @frannfyne


Style Notes: It's like floral midi dresses and knee-high boots were destined to be worn together, and Frann has absolutely nailed the look.

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5. Party Dress + Pointed Boots


(Image credit: @annabelrosendahl)

Style Notes: Planning your after-dark attire for an upcoming event or dinner? No need for ankle-baring stilettos—a pair of pointed boots with a narrow heel will complement your going-out dresses.

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6. Mini Dress + Western Boots


(Image credit: @francescasaffari)

Style Notes: Mini dresses and knee-highs are a popular pairing, and we especially love how Francesca has mixed things up with a cowboy-inspired pair.

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7. Black Maxi Dress + Slouch Boots


(Image credit: @alexisforeman wearing Inwear)

Style Notes: A simple black dress and boots is a winning combo. Add a tailored jacket over the top like Alexis did for added polish. 

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8. Animal-Print Dress + Chunky Boots


(Image credit: @emmarosestyle)

Style Notes: The fashion world's affinity for animal print will never waver. Right now, we're wearing our leopard- and zebra-adorned dresses with chunky lug-soled boots. Cool, right?

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This story was originally published at an earlier time and has since been updated.

Next Up: 6 Simple Outfits You Can Count on in Cold January Weather

Freelance Fashion Editor

Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at print and digital publications in Berlin and London, including Dazed & Confused and Indie magazine.

A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.

In her spare time, Bébhinn enjoys perusing Edinburgh’s best vintage shops, working through her out-of-control book collection and watching dog reels on Instagram.