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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 Impressum

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Dressy Leggings Outfits: 20+ 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. 27 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

With cream · 18 looks

Jumper, leggings & Chelsea boots
€915*
For cool days, about 5–12°C · Smart casual · 4 pieces from €75*
Red cardigan, taupe jumper & leggings
€866*
For cool days, about 5–12°C · Smart casual · 5 pieces from €75*
Cardigan, cream roll neck & navy leggings
€406*
For cool days, about 5–12°C · Everyday · 4 pieces from €60*
Yellow cardigan, taupe jumper & leggings
€786*
For cool days, about 5–12°C · Smart casual · 5 pieces from €75*
Red cardigan, taupe jumper & leggings
€875*
For cool days, about 5–12°C · Everyday · 5 pieces from €75*
Green cardigan, taupe jumper & black leggings
€1,157*
For cool days, about 5–12°C · Date night · 5 pieces from €181*

With red · 15 looks

Red cardigan, navy top & leggings
€416*
For mild days, about 12–20°C · Everyday · 5 pieces from €75*
Burgundy cardigan, burgundy jumper & black leggings
€1,054*
For cool days, about 5–12°C · Date night · 5 pieces from €181*
Black shirt, black leggings & ballet flats
€1,015*
For mild days, about 12–20°C · Smart casual · 4 pieces from €180*
Jumper, leggings & Chelsea boots
€1,000*
For cool days, about 5–12°C · Smart casual · 4 pieces from €75*

With black · 14 looks

Green cardigan, black jumper & black leggings
€1,189*
For cool days, about 5–12°C · Date night · 5 pieces from €181*
Cream cardigan, pink jumper & black leggings
€1,089*
For cool days, about 5–12°C · Date night · 5 pieces from €159*
Tan puffer jacket, brown shirt & grey leggings
€1,230*
For cool days, about 5–12°C · Everyday · 5 pieces from €160*
Cream cardigan, green jumper & black leggings
€1,814*
For cool days, about 5–12°C · Date night · 5 pieces from €181*
Black jacket, black jumper & black leggings
€1,169*
For cool days, about 5–12°C · Smart casual · 4 pieces from €180*

All looks

Filters

Budget for the whole look

Style

Colour

Season

One checkoutEvery piece from the same store

27 looks

Filter by brand in search

Red cardigan, tee & leggings

€335* · Pieces from €75*

For mild days, about 12–20°C · Everyday · 4 pieces from €75*

Would you wear it?

Gobi Cashmere · €199

Gobi Cashmere · €119

Gobi Cashmere · €181

Morrison · €99

Charcoal gilet, burgundy jumper & white leggings

€598* · Pieces from €99*

For cool days, about 5–12°C · Date night · 4 pieces from €99*

Would you wear it?

Gobi Cashmere · €159

Gobi Cashmere · €181

Gobi Cashmere · €199

Gobi Cashmere · €59

Red sweatshirt, white leggings & beige trainers

€598* · Pieces from €159*

For cool days, about 5–12°C · Everyday · 4 pieces from €159*

Would you wear it?

Gobi Cashmere · €159

Gobi Cashmere · €181

Gobi Cashmere · €199

Gobi Cashmere · €79

Green sweatshirt, white leggings & beige trainers

€618* · Pieces from €159*

For cool days, about 5–12°C · Everyday · 4 pieces from €159*

Would you wear it?

Gobi Cashmere · €259

Gobi Cashmere · €159

Gobi Cashmere · €181

Rothy's · €315

Cardigan, pink jumper & black leggings

€914* · Pieces from €159*

For cool days, about 5–12°C · Date night · 4 pieces from €159*

Good American · €135

Good American · €160

Good American · €91

Rothy's · €180

Rothy's · €280

Khaki jacket, jumper & navy leggings

€846* · Pieces from €91*

For cool days, about 5–12°C · Everyday · 5 pieces from €91*

Good American · €135

Good American · €120

Good American · €91

Rothy's · €315

Rothy's · €183

Cardigan, cream roll neck & navy leggings

€844* · Pieces from €91*

For cool days, about 5–12°C · Everyday · 5 pieces from €91*

Good American · €160

Good American · €185

Good American · €91

Rothy's · €180

Rothy's · €150

Navy jacket, green jumper & navy leggings

€766* · Pieces from €91*

For cool days, about 5–12°C · Everyday · 5 pieces from €91*

Rouje · €195

Rouje · €165

Rothy's · €101

Rothy's · €430

Red cardigan, jumper & leggings

€966* · Pieces from €75*

For cool days, about 5–12°C · Smart casual · 5 pieces from €75*

Rouje · €175

Rouje · €165

Rothy's · €91

Rothy's · €260

Yellow cardigan, taupe jumper & leggings

€766* · Pieces from €75*

For cool days, about 5–12°C · Smart casual · 5 pieces from €75*

Good American · €135

Good American · €195

Good American · €91

Rothy's · €190

Rothy's · €150

Khaki jacket, pink roll neck & navy leggings

€761* · Pieces from €91*

For cool days, about 5–12°C · Everyday · 5 pieces from €91*

Good American · €135

Good American · €160

Good American · €91

adidas · €120

Cardigan, white jumper & navy leggings

€602* · Pieces from €91*

For cool days, about 5–12°C · Everyday · 5 pieces from €91*

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: Cardigans or jackets
Shoes: Flats & mules or boots
Colours that work: Cream, red, black and navy
A whole look: €618–€1,054, typically €866

How these dressy leggings outfits come together

Counted from 27 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

Colours that work

Cream, red, black and navy 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 €618 and €1,054; the typical one is €866. Swap any piece to change the total.

Brands in these looks

Most pieces come from Rothy's, Rouje, Gobi Cashmere, Good American and Paez. Each look checks out on the stores' own sites, one store at a time.