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Discover Search

New looks, once a week

A few complete outfits picked from what's new. No account needed, unsubscribe any time.

Email address

Outfit ideas Brands Christmas party outfits What to wear with white trainers Women's date night outfits Men's work outfits Autumn outfits Winter outfits Streetwear outfits Minimalist outfits Women's workout outfits Men's smart casual outfits Outfits under £100 Outfits under £200

Wholefit is an independent outfit recommendation site. It isn't affiliated with or endorsed by the brands it shows, and you buy each piece on the site of the store that sells it. No store or brand pays us a commission yet; when one does, it won't decide what we recommend. * Prices include VAT, plus each store's delivery charges. Each piece is sold by the store named on its page.

About Privacy Policy Your Privacy Choices Terms of Use Affiliate Disclosure Brands & Copyright Accessibility Contact

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Dressy Leggings Outfits: 50+ Head-to-Toe Looks · Wholefit

Outfits / Dressy leggings outfits

Dressy leggings outfits

How to dress up leggings: plain black, brown or grey leggings under a long jumper, cardigan or blazer, with boots, loafers or ballet flats instead of trainers. 50 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

With black · 37 looks

Fleece, olive top & brown leggings
£329*
For cool days, about 5–12°C · Everyday · 4 pieces from £42*
Purple gilet, tee & black leggings
£309*
For mild days, about 12–20°C · Everyday · 5 pieces from £34*
Pink jumper, leggings & grey boots
£330*
For cool days, about 5–12°C · Smart casual · 4 pieces from £50*
Green jacket, brown jumper & black leggings
£620*
For cool days, about 5–12°C · Smart casual · 4 pieces from £85*
Grey jacket, jumper & black leggings
£970*
For cool days, about 5–12°C · Smart casual · 5 pieces from £100*
Brown jacket, red jumper & black leggings
£810*
For cool days, about 5–12°C · Smart casual · 5 pieces from £85*

With brown · 24 looks

Black jacket, blue jumper & black leggings
£625*
For cool days, about 5–12°C · Smart casual · 4 pieces from £85*
Grey jacket, jumper & black leggings
£845*
For cool days, about 5–12°C · Smart casual · 4 pieces from £100*
Cream gilet, yellow jumper & black leggings
£367*
For cool days, about 5–12°C · Smart casual · 4 pieces from £38*
Pink cardigan, cream jumper & brown leggings
£501*
For cool days, about 5–12°C · Smart casual · 5 pieces from £20*
Black jacket, yellow jumper & brown leggings
£618*
For cool days, about 5–12°C · Everyday · 5 pieces from £85*
Gilet, black jumper & brown leggings
£410*
For cool days, about 5–12°C · Smart casual · 5 pieces from £46*

With grey · 20 looks

Black fleece, olive hoodie & black leggings
£533*
For cool days, about 5–12°C · Everyday · 5 pieces from £52*
Cardigan, white jumper & navy leggings
£620*
For cool days, about 5–12°C · Everyday · 5 pieces from £75*
Cardigan, jumper & leggings
£448*
For cool days, about 5–12°C · Smart casual · 5 pieces from £25*
Black gilet, olive top & black leggings
£785*
For mild days, about 12–20°C · Everyday · 5 pieces from £34*
Grey jacket, black roll neck & black leggings
£740*
For cool days, about 5–12°C · Smart casual · 5 pieces from £100*
Grey jacket, jumper & black leggings
£845*
For cool days, about 5–12°C · Smart casual · 4 pieces from £100*

With cream · 18 looks

Black jacket, jumper & black leggings
£647*
For cool days, about 5–12°C · Smart casual · 5 pieces from £85*
Cardigan, black tee & black leggings
£463*
For mild days, about 12–20°C · Everyday · 5 pieces from £42*
Cardigan, cream roll neck & navy leggings
£712*
For cool days, about 5–12°C · Everyday · 5 pieces from £75*
Khaki jacket, jumper & navy leggings
£624*
For cool days, about 5–12°C · Everyday · 5 pieces from £75*
Black roll neck, black leggings & Uggs
£419*
For cool days, about 5–12°C · Smart casual · 4 pieces from £100*
Green corduroy jacket, cream jumper & navy leggings
£604*
For cool days, about 5–12°C · Everyday · 5 pieces from £75*

All looks

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One checkoutEvery piece from the same store

50 looks

Filter by brand in search

Morrison · £99

Fleece, olive hoodie & black leggings

£285* · Pieces from £52*

For cool days, about 5–12°C · Everyday · 4 pieces from £52*

Would you wear it?

Rothy's · £96

Brown gilet, grey hoodie & navy leggings

£253* · Pieces from £44*

For mild days, about 12–20°C · Everyday · 4 pieces from £44*

Would you wear it?

Rothy's · £76

Burgundy jacket, black top & black leggings

£290* · Pieces from £36*

For cool days, about 5–12°C · Everyday · 4 pieces from £36*

Would you wear it?

Rothy's · £76

Top, black leggings & flats

£183* · Pieces from £48*

For mild days, about 12–20°C · Everyday · 3 pieces from £48*

Would you wear it?

Barbour · £66

Cardigan, jumper & leggings

£179* · Pieces from £25*

For cool days, about 5–12°C · Everyday · 4 pieces from £25*

Colorful Standard · £90

Carhartt · £110

Pink jumper, leggings & Uggs

£350* · Pieces from £50*

For cool days, about 5–12°C · Smart casual · 4 pieces from £50*

Sporty & Rich · £195

Sporty & Rich · £195

Sporty & Rich · £130

Morrison · £99

Cream cardigan, cream hoodie & grey leggings

£619* · Pieces from £99*

For cool days, about 5–12°C · Everyday · 4 pieces from £99*

Finisterre · £210

Finisterre · £125

Finisterre · £85

Rothy's · £155

Green jacket, navy jumper & brown leggings

£575* · Pieces from £85*

For cool days, about 5–12°C · Smart casual · 4 pieces from £85*

Pangaia · £195

Pangaia · £100

Rothy's · £155

Rothy's · £125

Black jumper, black leggings & green clogs

£575* · Pieces from £100*

For cool days, about 5–12°C · Smart casual · 4 pieces from £100*

Finisterre · £295

Finisterre · £155

Finisterre · £85

Rothy's · £265

Jacket, cream jumper & black leggings

£800* · Pieces from £85*

For cool days, about 5–12°C · Smart casual · 4 pieces from £85*

Finisterre · £180

Finisterre · £135

Finisterre · £85

Black jacket, green jumper & black leggings

£545* · Pieces from £85*

For cool days, about 5–12°C · Everyday · 4 pieces from £85*

Rothy's · £265

Rothy's · £220

Corduroy jacket, jumper & leggings

£628* · Pieces from £25*

For cool days, about 5–12°C · Smart casual · 5 pieces from £25*

Finisterre · £165

Finisterre · £155

Finisterre · £85

Clarks Originals · £165

Blue jacket, cream jumper & brown leggings

£570* · Pieces from £85*

For cool days, about 5–12°C · Smart casual · 4 pieces from £85*

Pangaia · £285

Pangaia · £195

Pangaia · £100

Clarks Originals · £165

Carhartt WIP · £95

Black jacket, jumper & black leggings

£840* · Pieces from £100*

For cool days, about 5–12°C · Smart casual · 5 pieces from £100*

Finisterre · £210

Finisterre · £145

Finisterre · £85

Rothy's · £150

Rothy's · £235

Black jacket, brown jumper & brown leggings

£825* · Pieces from £85*

For cool days, about 5–12°C · Smart casual · 5 pieces from £85*

Rothy's · £150

Cardigan, jumper & leggings

£263* · Pieces from £25*

For cool days, about 5–12°C · Smart casual · 4 pieces from £25*

Rothy's · £265

Corduroy jacket, jumper & leggings

£408* · Pieces from £25*

For cool days, about 5–12°C · Smart casual · 4 pieces from £25*

More outfit ideas

Women's dressy leggings outfits
Christmas party outfits
Office Christmas party outfits
Christmas outfits
New Year's Eve outfits
Après-ski outfits
5 degree weather outfits
10 degree weather outfits
Casual winter outfits
Winter work outfits
Business casual outfits
Winter date night outfits

Dressy leggings outfits at a glance

On top: Knitwear or t-shirts & tops
Layers: Jackets or cardigans
Shoes: Flats & mules or boots
Colours that work: Black, brown, grey and cream
A whole look: £367–£647, typically £575

How these 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: Jackets or cardigans
Shoes: Flats & mules or boots

Colours that work

Black, brown, grey and cream 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 £367 and £647; the typical one is £575. Swap any piece to change the total.

Brands in these looks

Most pieces come from Rothy's, Finisterre, Tala, Pangaia and UGG. Each look checks out on the stores' own sites, one store at a time.