I'm After a Cosy Yet Chic Outfit—These 6 Jumper-Dress and Boots Looks Work

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


(Image credit: @mariaalia)

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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2. Cable-Knit Jumper Dress + Heeled Boots


(Image credit: @annabelrosendahl)

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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3. Form-Fitting Dress + Snakeskin Boots


(Image credit: @aimeesong)

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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4. Chocolate Brown Dress + Matching Boots


(Image credit: @anoukyve)

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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5. Split-Leg Dress + Cowboy Boots


(Image credit: @samantheah)

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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6. Belted Dress + Lug-Sole Boots


(Image credit: @emmarosestyle)

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

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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

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.