Jumper dresses are the ultimate winter comfort piece. They’re cosy, flattering, and ridiculously easy to wear when you can’t face the thought of coordinating separates. Add winter boots, and you’ve got a foolproof outfit that works for everything from lazy weekends to work meetings to casual nights out.
But you need to choose the right boot style to complement your jumper dress length and vibe. Here are the best jumper dress and boot combinations to get you through winter in style and comfort.
Chunky boots combos
Chunky boots with jumper dresses create that perfect balance between cosy and edgy. The thicker boot grounds the softness of the knitwear beautifully and looks effortlessly cool.
Oversized grey or oatmeal jumper dress
- Throw on a black biker jacket for a slightly grunge, “I tried but not too hard” vibe
- Add a crossbody and minimal jewellery to keep it simple
shoezone pick: Lilley Womens Black Lace Up Ankle Boot
Burgundy or forest green jumper dress
- Style with semi-opaque black tights and dark green or black combat boots
- Add a long wool coat for a polished ‘city’ look
- Seasonal and sophisticated, but not too dressy
shoezone pick: Lilley Womens Black Chunky Buckle Ankle Boot
Cable-knit cream jumper dress
- Include a skinny scarf or leg warmers for a nod to the on-trend indie and ballet-core aesthetic
- Add a wool coat or oversized cardigan for extra warmth
shoezone pick: Lilley Womens Black Patent Zip Up Boot
Knee-high boots combos
Knee-high boots with jumper dresses create an elegant silhouette that works for smarter occasions while still being professional and practical.
Fitted ribbed jumper dress (midi length)
- Throw on a trench coat or tailored long coat
- Smart enough for work and transitions easily to evening plans
shoezone pick: Lilley Womens Black Heeled Knee High Boot
Taupe or camel jumper dress
- Add a wool fedora or simple beanie
- Keep jewellery simple with gold pieces that complement the warm tones
shoezone pick: Lilley Womens Tan Knee High Boots
Black turtleneck jumper dress
- Wear with sheer or semi-opaque tights and pointed-toe knee-high boots
- Add a statement coat or a simple leather jacket
- All-black combos are sleek, sophisticated, and chic – perfect for dinner or drinks
shoezone pick: Truffle Collection Romina Womens Black Heeled Boot
Ankle boots combos
Ankle boots are the best all-rounder footwear when it comes to styling jumper dresses. They work with every dress length and style, and are comfortable enough for all-day wear.
Straight-cut midi jumper dress
- Layer with a long camel coat
- Add a structured bag and simple jewellery to complete the low-key ‘expensive’ look
shoezone pick: Lilley Womens Black Block Heel Ankle Boot
Chocolate brown jumper dress
- Keep jewellery simple (gold hoops, a watch)
- Warm textures and tones make the look feel cosy and approachable
shoezone pick: Lilley Womens Tan Chelsea Boot
Soft merino jumper dress
- Pair with opaque tights and more fitted ankle boots
- Choose a cropped puffer or bomber jacket to balance proportions
- Ideal for running errands, casual meet-ups, or days when you’re on your feet a lot
shoezone pick: Lilley Womens Black Ankle Boots
Quick jumper dress and boots outfit ideas
| Jumper dress style |
Boots style |
Extras that make it current |
| Oversized grey mini |
Black combat boots |
Black tights, biker jacket, skinny scarf |
| Ribbed black mini |
Sleek knee-high boots |
Opaque tights, long tailored coat |
| Cream cable-knit mini |
Chunky lace-up boots |
Thick tights, leg warmers or skinny scarf |
| Merino midi (neutral) |
Slim black ankle boots |
Long camel coat, minimal gold jewellery |
| Striped jumper dress |
Platform Chelsea boots |
Bomber or denim jacket |
Styling tips for jumper dresses and boots
Think about proportions
Oversized jumper dresses work best with chunkier boots or knee-highs that add structure. More fitted jumper dresses pair well with sleeker ankle boots or pointed-toe styles.
Add definition
If your jumper dress is quite loose or boxy, add a belt to define your waist. This stops the outfit from looking shapeless and creates a more flattering silhouette.
Layer thoughtfully
Coats, jackets, and cardigans can completely change the vibe of a jumper dress outfit. A biker jacket adds edge, a tailored coat adds polish, and an oversized cardigan keeps things casual and cosy.
Choose the right tights
Thick opaque tights feel more intentional and winter-appropriate than sheer styles. Match your tight colour to your boots for a leg-lengthening effect, or create contrast with lighter tights if you want to break up the silhouette.
Consider dress length
Mini jumper dresses work well with knee-high boots or chunky ankle boots. Midi jumper dresses pair beautifully with ankle boots or sleek knee-highs. The goal is to avoid awkward gaps or too much bare leg showing in winter weather.
Accessorise appropriately
Simple jewellery (gold hoops, delicate necklaces) keeps the focus on the outfit rather than competing with it. Add a scarf, beanie, or hat for extra warmth and style points.
How to choose the right jumper dress
For petite frames
Opt for fitted or semi-fitted styles rather than very oversized ones, which can swamp smaller builds. Midi lengths often work better than maxis.
For taller heights
You can pull off longer midi and maxi jumper dresses beautifully. Just make sure they're actually long enough and don't end at an awkward mid-calf length.
For curvy figures
Look for jumper dresses with some structure or shape, or add a belt to define your waist. Very loose, shapeless styles can be unflattering, regardless of size.
For everyone
Choose good quality knitwear that won't pill or lose shape after one wash. Merino, cashmere blends, and quality acrylic knits all work well. Avoid very thin knits that go see-through or shapeless after wearing.
Wrapping up
Jumper dresses and boots are one of winter’s easiest and most comfortable outfit combos. With the right pairing, getting dressed in winter becomes a lot more stress-free.
Explore shoezone's collection of women's winter boots to find your perfect jumper dress companion.
Check out the shoezone blog for more style tips and footwear suggestions for every occasion.