Whilst winter comes with its fashion struggles, it does offer a moment to indulge in one of my favourite styling combinations: boots and dresses. Bored of wearing trousers all the time, I've been looking for the opportunity to re-introduce dresses to my wardrobe rotation. With this in mind, it's time to debut my favourite outfit combination.
I'm keen to add tights to my outfit rotations but for now, I don't need a layer quite so heavy, so I find myself reaching for knee-high boots specifically for this purpose. Not only are they the most polished boot silhouette (in my opinion), but they're also totally timeless and work well with every dress trend I can think of. For midis, they disappear under the fabric to create a seamless finish where ankle boots wouldn't. With miniskirts, they look inherently cool and work to balance out the short hemline.
Truly, dresses and knee-high boots make a perfect pairing, and I'm not the only one who thinks so. I keep daily tabs on what's being searched for on Google, and whilst there are a surprising amount of queries around air fryers and iPads, amongst the tech and kitchen gadgetry, I can see the term "dresses with knee boots" is up by 100% since last week. Assuming, then, that you're on the hunt for some dresses-with-knee-high-boots outfits to wear right now, I've assembled seven looks below that perfectly demonstrate how handy this pairing is. From minis to midis and heels to flats, scroll on to see the chicest ways to style the combination this winter.
7 DRESSES AND KNEE-HIGH BOOTS OUTFITS TO TRY:
1. KNITTED ROLL-NECK + SQUARE-TOE BOOTS
Style Notes: When those cold-weather days arrive, you'll be grateful for a chunky knit dress to keep you warm. Opt for a neutral shade to look put-together and add some chic square-toe boots.
Shop the Look:
I love this belted style.
I have these and they're so comfortable.
2. SILK DRESS + STILETTO BOOTS
Style Notes: Giving her heeled boots an even more elegant spin, influencer and stylist Sylvie Mus styled them here with a refined silk dress for an evening out in Paris. Retaining a sophisticated silhouette, the boots pairing added warmth and height to her evening outfit without distracting from the dress.
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Supremely elegant.
Style with a pleated mini or wear with a silk maxi.
3. DRAPED DRESS + KITTEN HEEL BOOTS
Style Notes: Draped dresses always look sophisticated and this is especially true when you pair them with kitten-heel boots. Wear on its own or opt for a chunky belt if you really want to dress it up.
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The perfect evening style.
You'll reach for these year round.
4. KNIT DRESS + BROWN BOOTS
Style Notes: When the sunshine isn't playing ball, reach for a cosy kitted dress and trending brown boots to see you through. Insulating you from those unexpected biting breezes, this comfortable combination will nod towards a major colour trend whilst keeping you snug in the process.
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Who can resist a cosy dress?
The brown boot trend is one of my favourite to arise over the past six months.
5. MINIDRESS + KNEE-HIGH BOOTS
Style Notes: Channel the spirit of summer and pull out your favourite flirty mini a little early this season. To close the temperature gap whilst it's still winter, style with warm tights and knee-high boots—and don't be afraid to keep a maxi wool coat close to hand.
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I come back to Ganni season after season for its joy-sparking dresses.
Black, pointed-toe boots are one of the most versatile pairs to have in your arsenal.
6. PINAFORE DRESS + COWBOY BOOTS
Style Notes: A pinafore dress is a summer staple, but with a heavy layer thrown into the mix, you can get your wear out of it during wintertime too. Style with chunky cowboy boots to toughen up the "feminine dress" and add some tights if there's a breeze in the air.
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Every great wardrobe starts with an easy layering piece, and this is a personal favourite.
Wear over a white tee, chunky roll-neck or crisp cotton button-down.
These embroidered cowboy boots top so many wish lists.
7. WHITE MAXI DRESS + RIDING BOOTS
Style Notes: Tap into the returning boho trend by way of a few key buys. A draped white maxi dress will instill effortless energy and a knee-high boot pairing will add a relaxed edge whilst working to polish the look. For extra points layer on gold necklaces and you'll have achieved a very 2024 take on the late '00s throwback.
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Style with pared-back loafers or wear with your favourite knee-highs.
Drawing on equestrian inspiration, these boots are an easy way to add some interest into your day-to-day wardrobe.
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