I'm After a Cosy Yet Chic Outfit—These 7 Jumper-Dress-and-Boot Looks Work
Humaa Hussain
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.
Shop the Look:
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).
Shop the Look:
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.
Shop the Look:
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.
Shop the Look:
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.
Shop the Look:
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.
Shop the Look:
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.
Shop the Look:
This story was published at an earlier time and has since been updated.
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 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.
- Humaa HussainJunior Branded Content Editor
-
The Brutally Honest Skincare Advice You Needed to Know Yesterday, According to 2 Beauty Industry Vets
The Dieux founders share their hot takes and unfiltered product recs.
-
Sorry to My Classic Black Shoes, But This Printed Shoe Trend Is Defining Fall 2025
Spotted on fashion people in Venice, NYC, and Copenhagen.
-
These 32 Chic Zara Fall 2025 Shoe Finds Are the Key to Looking Like a Fashion Person—Good Luck Picking Just One Pair
Prepare for endless compliments.
-
Here You Go: 5 Trend-Forward Fall Outfit Ideas I Think Are Wildly Chic
These looks get a yes.
-
Blue Jeans Are Fine, But for Fall, Chic People Know This Controversial Denim Trend Looks Richer
Hot take incoming…
-
I'm a Fashion Editor on a Budget—27 Incredibly Chic Fall Finds That Will Get You More Bang for Your Buck
Stellar under-$150 finds right this way.
-
Soft Knits and Suede Boots Are on My Mind—Here's What's in My Nordstrom Cart
Get in the fall mood with these chic picks.
-
5 Chic End-of-Summer Denim Outfits That Will Make You Look Like a Fashion Person
From Stockholm to Paris to London.
-
The "No White After Labor Day" Rule Is Out—These Chic Outfits Are In
Who says white has to have a season? We’re wearing it all year long.
-
The Chic 2-Piece Outfit Busy Fashion People Always Wear in September
Awkward weather, conquered.