Yellow sweater, grey leggings & navy flats
$440For cool days, about 40–55°F · Smart casual · 4 pieces from $60
Women's dressy leggings outfits
How to dress up leggings: plain black, brown or grey leggings under a long sweater, cardigan, shirt or blazer that covers the hips, with ankle boots, knee boots, loafers or flats instead of trainers. Add a coat in winter. 100 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026
Women's dressy leggings outfits at a glance
- On top
- Knitwear or t-shirts & tops
- Layers
- Cardigans or jackets
- Shoes
- Flats & mules or boots
- A whole look
- $340–$577, typically $416
With black · 72 looks
Jacket, green sweater & black leggings
$416For cool days, about 40–55°F · Smart casual · 4 pieces from $25
Charcoal denim jacket, blue sweater & black leggings
$353For cool days, about 40–55°F · Smart casual · 5 pieces from $45
Green cardigan, grey sweater & brown leggings
$373For cool days, about 40–55°F · Smart casual · 5 pieces from $45
Blue cardigan, cream sweater & grey leggings
$423For cool days, about 40–55°F · Smart casual · 4 pieces from $39
Purple cardigan, grey sweater & black leggings
$454For cool days, about 40–55°F · Smart casual · 4 pieces from $78
With grey · 47 looks
With cream · 43 looks
With green · 33 looks
All looks
100 looks
Filter by brand in searchCream cardigan, grey tee & leggings
$287For cool days, about 40–55°F · Everyday · 4 pieces from $39
Would you wear it?
Cream polo, grey leggings & burgundy flats
$232For mild days, about 55–70°F · Smart casual · 4 pieces from $16
Would you wear it?
Blue cardigan, white tee & black leggings
$200For mild days, about 55–70°F · Everyday · 5 pieces from $34
Would you wear it?
Navy sweatshirt, purple leggings & beige boots
$152For cool days, about 40–55°F · Everyday · 3 pieces from $35
Would you wear it?
Brown bomber jacket, blue sweater & grey leggings
$340For cool days, about 40–55°F · Everyday · 5 pieces from $45
Green cardigan, grey sweater & black leggings
$349For cool days, about 40–55°F · Smart casual · 4 pieces from $45
Jacket, green sweater & black leggings
$558For cool days, about 40–55°F · Smart casual · 5 pieces from $25
Grey jacket, black sweater & black leggings
$938For cool days, about 40–55°F · Smart casual · 4 pieces from $140
Olive jacket, shirt & black leggings
$577For cool days, about 40–55°F · Smart casual · 5 pieces from $25
Green cardigan, sweater & black leggings
$669For 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
Black top, black leggings & burgundy boots
$135For mild days, about 55–70°F · Everyday · 3 pieces from $41
Puffer jacket, charcoal top & grey leggings
$918For cold days, about 25–40°F · Everyday · 5 pieces from $58
Pink sweater, black leggings & grey boots
$653For cool days, about 40–55°F · Smart casual · 4 pieces from $120
Grey cardigan, blue sweatshirt & leggings
$583For cool days, about 40–55°F · Everyday · 5 pieces from $39
Jacket, green sweater & black leggings
$606For cool days, about 40–55°F · Smart casual · 5 pieces from $25
Green cardigan, sweater & brown leggings
$438For cool days, about 40–55°F · Smart casual · 5 pieces from $54
How these women's dressy leggings outfits come together
Counted from 41 of these looks.
The pieces that come up most
- On top
- Knitwear or t-shirts & tops
- Layers
- Cardigans or jackets
- Shoes
- Flats & mules or boots
Colors that work
Black, grey, cream and green 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 $340 and $577; the typical one is $416. 32 include a piece on sale. Swap any piece to change the total.
Brands in these looks
Most pieces come from tentree, Thursday Boots, Reebok, Mia and Everlane. Each look checks out on the stores' own sites, one store at a time.