7 Elegant Dress-and-Boot Outfits Stylish Women in London and Copenhagen Are Wearing Instead of Jeans This Winter
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.
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2. MINI JUMPER DRESS + RIDING BOOTS
Style Notes: Tap into the returning jumper dress trend by way of a few key buys. A mini knit dress in a fun colour will instill effortless energy and a knee-high boot and long sock pairing will add a relaxed edge whilst working to polish the look.
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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.
3. 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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4. 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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5. 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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The brown boot trend is one of my favourite to arise over the past six months.
6. 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 Nobody's Child season after season for its joy-sparking dresses.
Black, pointed-toe boots are one of the most versatile pairs to have in your arsenal.
7. 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.
Natalie Munro is Who What Wear UK’s news writer. Having worked in the fashion industry since her time at university—where she obtained a BA in Journalism from University of the Arts London, Natalie's experience spans journalistic and styling roles. In the early stages of her career Natalie predominately worked on editorial shoots for fashion publications such as British Vogue, Vogue Ukraine, AnOther Magazine and Elle UK, before moving into journalism roles.
On completion of her degree she interned in the editorial team at British Vogue and later went on to freelance for the publication. Here, she developed her interest in reporting on the latest fashion news and trends. Inspired by the dynamic nature of the industry, Natalie went on to write for other lifestyle and fashion brands and publications before taking on the role as News Writer for Who What Wear.
With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Focusing on trends on and off the runway, as well as street style and celebrity fashion, Natalie reports on a daily basis, ensuring that she remains ahead of the trends. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.
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