9 Easy Dress-and-Boot Outfits That Make January Dressing Totally Effortless

There are so many dress trends to get excited about this year. From preppy minis to pale pink maxis, the S/S 25 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.

Dress-and-Boot Combos That Work Every Time:

1. Neutral Knitted Dress + White Boots

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

Style Notes: Hands up if you struggle to style slip dresses in January. 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

Style Notes: This punchy combination feels very fresh for 2025. 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

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 + Statement Boots

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

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6. Mini Dress + Western Boots

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

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

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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9. Mini Knitted Dress + Riding Boots

Style Notes: Don't shy away from minis just because it's cold outside. Opt for a knitted iteration and add some tall riding boots to keep you legs warm and cosy all day.

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