Winter Has Arrived—6 Jumper-Dress-and-Boots Outfits That Are Chic Yet Cosy

If there's one thing all the Who What Wear editors agree on, it is that jumper dresses work as if by magic, making us look effortlessly put together yet offering unparalleled comfort. Trust me, once you're clued into this cosy staple, you'll struggle to wear anything else. 2022 was the year we all fell back in love with knitted dresses, and we're certainly not ready to let go of the rekindled obsession anytime soon. Especially with divine new iterations from Khaite and Cristopher Esber being released on the regular.

At this time of year, boots are a sensible teammate. These cold-weather allies have a lot in common, both promising to beat the chill and keep you looking on-point in the process. Trainers work great with jumper dresses in transitional periods, but let's be realistic: only boots and fluffy socks can keep our toes sufficiently toasty in the midst of winter.

This isn't purely a practical pairing—it turns out boots and knit dresses are an aesthetic match made in heaven, too. From cowboy designs to suede knee-highs, every shape and silhouette seems to complement this dress style. That being said, certain combinations really grabbed our attention when we spotted them on Instagram. Keep scrolling to see the best jumper-dress-and-boots outfits of the bunch.

1. Midi Dress + Knee-High Boots

6 Perfect Jumper-Dress–and-Boots Outfits: @mariaalia in a midi dress and knee-high boots



Style Notes: Knee-high boots peeking out from under a midi dress is such a good look. I'm particularly fond of this navy-and-burgundy colour palette.

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Trust COS to make one of the most versatile dresses around.

This simple belt holds the power to totally transform an outfit.

Personally, I love the matte navy version of this iconic bag.

Burgundy boots are arguably just as classic as black or brown.

2. Cable-Knit Jumper Dress + Heeled Boots

Style Notes: When it's bitingly cold outside, a thick cable-knit jumper dress should do the trick (particularly if you wear an extra layer on top, like Anabel).

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Bundle up from the cold in this cosy style.

Our editors really rate & Other Stories' outerwear.

It's worth spending a little more on a high-quality tote.

3. Form-Fitting Dress + Snakeskin Boots

6 Perfect Jumper-Dress–and-Boots Outfits: @aimeesong in a tight knitted dress and printed boots



Style Notes: Sleek snakeskin boots make this elegant dress option look a touch edgier. Choose a heeled pair for smarter occasions.

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This could easily be dressed up for an evening out.

4. Chocolate Brown Dress + Matching Boots

6 Perfect Jumper-Dress–and-Boots Outfits: @anoukyve in a chocolate brown dress with matching boots



Style Notes: Chocolate brown will be ubiquitous throughout winter 2023, just like last year. Create a top-to-toe tonal look with matching boots and a rich brown bag.

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Dresses like this almost make me excited for cold weather.

Keep this on-hand at all times—it'll go with absolutely everything.

Everyone's going to be wearing silver jewellery this season.

Wear with dresses, skirts, jeans and leggings. They'll look cool every time.

5. Split-Leg Dress + Cowboy Boots

6 Perfect Jumper-Dress–and-Boots Outfits: @samantheah in a split leg dress and cowboy boots



Style Notes: If you're going to wear cowboy boots, you might as well show them off. Choose a split-leg knitted dress to really let them shine.

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There are so many leather jackets to get excited about this autumn/winter.

Throw this dress on and you'll look polished instantly.

I'm still searching for the perfect cowboy boots—this traditional pair comes pretty close.

6. Belted Dress + Lug-Sole Boots

Style Notes: Nip your waist in and juxtapose this flattering silhouette with chunky boots on the bottom.

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This versatile piece can be worn multiple different ways.

The chunky boot trend is showing no sign of slowing down, and these are about as chunky as it gets.

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

Next up: I Love a Chic Black Dress—These Are the 23 Styles Worth Bookmarking for Winter