Jacket, green sweater & black leggings
$606For cool days, about 40–55°F · Smart casual · 5 pieces from $25
Women's winter leggings outfits
Winter leggings outfits: black or brown leggings under a chunky knit, oversized sweatshirt or long cardigan, with a puffer, wool coat or vest and ankle boots, knee boots or Uggs. 37 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026 · How to wear leggings in winter
With black · 27 looks
White jacket, white turtleneck & black leggings
$642For cool days, about 40–55°F · Smart casual · 4 pieces from $138
Grey jacket, black sweater & black leggings
$954For cool days, about 40–55°F · Smart casual · 4 pieces from $140
Green vest, grey sweater & black leggings
$546For cool days, about 40–55°F · Smart casual · 4 pieces from $78
Black jacket, black sweater & black leggings
$1,425For cool days, about 40–55°F · Smart casual · 5 pieces from $45
Olive jacket, charcoal sweater & black leggings
$559For cool days, about 40–55°F · Smart casual · 5 pieces from $25
With grey · 19 looks
With cream · 18 looks
How to wear leggings in winter
Are leggings warm enough for winter?
Regular leggings are thin, so on their own they're fine for short trips but not for a long day below about 40°F. Fleece-lined or thermal leggings are much warmer and look the same from outside. A long coat that covers the thighs and boots that cover the ankle make the biggest difference, and wool socks under the boots keep the cold from coming up through the soles.
What should I wear with leggings in winter?
Balance the slim leg with volume on top: a chunky sweater, an oversized sweatshirt, a long cardigan or a shirt jacket that covers the hips. Then a puffer, a wool coat or a quilted vest. Black, brown and charcoal leggings look the most like trousers; keep bright or patterned ones for the gym. A matching top, like a black knit over black leggings, makes the whole outfit look longer and smarter.
Which shoes go with leggings in winter?
Ankle boots and knee boots are the easiest: they cover the gap and look finished. Shearling boots like Uggs are the cozy option for errands. Chunky sneakers work on dry days. Ballet flats or loafers dress leggings up, but they're for indoors or a short walk.
How do I make leggings look put together?
Choose a thick, opaque pair that doesn't go shiny or see-through when you bend, add a top that covers the hips, and pick one smart piece, like a wool coat, leather boots or a structured bag. Avoid a full gym outfit unless you're on your way to the gym.
Can leggings be dressed up for winter?
Yes, within limits. Thick black leggings with a long fine-knit sweater or a sweater dress, a wool coat and knee boots look neat enough for lunch or a casual office. Add a scarf and a leather bag, and keep the sneakers for the weekend.
Questions people ask
Can I wear leggings to work in winter?
In a casual office, thick black leggings under a long sweater or a sweater dress with ankle boots can work. In a business casual office, trousers are safer.
Do you wear leggings with Uggs?
Yes, it's a classic winter weekend combination. Add a long sweater or a sweatshirt and a puffer or a long coat.
What coat goes with leggings?
A long puffer, a wool coat that falls to the knee or a quilted jacket: anything that covers the hips and keeps your thighs warm.
Are leggings or tights better under a dress in winter?
Tights look more finished under a dress; leggings work under a long sweater or a tunic that covers the hips.
All looks
37 looks
Filter by brand in searchPuffer jacket, charcoal top & grey leggings
$918For cold days, about 25–40°F · Everyday · 5 pieces from $58
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Cream jacket, cream sweater & navy leggings
$833For cold days, about 25–40°F · Smart casual · 5 pieces from $125
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White jacket, black sweater & black leggings
$859For cold days, about 25–40°F · Smart casual · 5 pieces from $138
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Black jacket, brown sweater & grey leggings
$793For cold days, about 25–40°F · Smart casual · 5 pieces from $128
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Cream jacket, cream sweater & black leggings
$909For cold days, about 25–40°F · Smart casual · 5 pieces from $128
White jacket, black sweater & black leggings
$904For cold days, about 25–40°F · Smart casual · 5 pieces from $138
Cream jacket, cream sweater & brown leggings
$840For cold days, about 25–40°F · Smart casual · 5 pieces from $144
Black jacket, white turtleneck & grey leggings
$2,529For cold days, about 25–40°F · Smart casual · 5 pieces from $128
Jacket, green sweater & black leggings
$558For cool days, about 40–55°F · Smart casual · 5 pieces from $25
Black jacket, sweater & black leggings
$835For cool days, about 40–55°F · Smart casual · 4 pieces from $45
Cream cardigan, grey tee & leggings
$287For cool days, about 40–55°F · Everyday · 4 pieces from $39
Grey cardigan, blue sweatshirt & leggings
$583For cool days, about 40–55°F · Everyday · 5 pieces from $39
How these women's winter leggings outfits come together
Counted from 30 of these looks.
The pieces that come up most
- On top
- Knitwear or t-shirts & tops
- Layers
- Jackets or cardigans
- Shoes
- Boots or flats & mules
Colors that work
Black, cream, grey and brown come up most often across these looks, so they make an easy base to build on.
What a complete look costs
Most whole outfits here cost between $558 and $954; the typical one is $833. 19 include a piece on sale. Swap any piece to change the total.
Brands in these looks
Most pieces come from Thursday Boots, Alo, Pangaia, Rothy's and Everlane. Each look checks out on the stores' own sites, one store at a time.