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. The past few years we've seen everyone fall 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
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 brown version of this iconic bag.
Black boots are arguably just as classic as 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 H&M' outerwear.
It's worth spending a little more on a high-quality tote.
Such a timeless boot.
3. Form-Fitting Dress + Snakeskin 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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An editor favourite.
This could easily be dressed up for an evening out.
Statement-makers, this one is for you.
4. Chocolate Brown Dress + 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
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 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.
7. Mini Knit Dress + Over The Knee Boots
Style Notes: A mini knit dress paired with over-the-knee boots creates a chic, leg-lengthening effect that's perfect for evenings out. Add structure with a tailored coat or leather jacket, and layer sheer tights for warmth and a touch of elegance.
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Grey and black is such an elite colour combo.
The belt is such a chic bonus.
Won't these look so good worn with dark wash jeans too?
7. Turtleneck Knit Dress + Riding Boots
Style Notes: Style a cosy turtleneck knit dress with sleek riding boots for a timeless, equestrian-inspired look. Finish with a belt to define the waist and a trench coat or blazer for added polish.
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Cute and cosy—it's a win, win
Toteme always gets boots right.
I love a silver buckle belt.
This story was published at an earlier time and has since been updated.
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