What to wear with a midi dress

Midi dress outfits for day and night, with boots, flats, heels and layers. 108 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

With black · 44 looks

Cream cardigan, black midi dress & brown clogs
£193*
For mild days, about 12–20°C · Date night · 3 pieces from £40*
Midi dress, black trainers & burgundy bag
£184*
For mild days, about 12–20°C · Everyday · 3 pieces from £30*
Black midi dress & Uggs
£188*
For mild days, about 12–20°C · Smart casual · 2 pieces from £93*
Burgundy midi dress & Uggs
£284*
For cool days, about 5–12°C · Smart casual · 2 pieces from £141*
Burgundy cardigan, black midi dress & Uggs
£299*
For mild days, about 12–20°C · Date night · 3 pieces from £95*
Brown jacket, blue midi dress & black trainers
£296*
For mild days, about 12–20°C · Everyday · 3 pieces from £88*

With cream · 32 looks

With red · 37 looks

With brown · 29 looks

All looks

108 looks

Red cardigan, beige midi dress & black trainers

£270*

For mild days, about 12–20°C · Everyday · 3 pieces from £83*

Would you wear it?

Jacket, brown midi dress & adidas Spezials

£175*

For mild days, about 12–20°C · Smart casual · 3 pieces from £35*

Would you wear it?

Tan jacket, burgundy midi dress & black trainers

£200*

For mild days, about 12–20°C · Smart casual · 3 pieces from £50*

Would you wear it?

Green gilet, beige midi dress & trainers

£295*

For cool days, about 5–12°C · Everyday · 3 pieces from £47*

Would you wear it?

Grey gilet, white midi dress & trainers

£172*

For mild days, about 12–20°C · Smart casual · 3 pieces from £32*

Black midi dress & trainers

£155*

For mild days, about 12–20°C · Date night · 2 pieces from £40*

Bomber jacket, midi dress & navy trainers

£289*

For cold days, about −5 to 5°C · Everyday · 3 pieces from £30*

Midi dress & penny loafers

£200*

For mild days, about 12–20°C · Smart casual · 2 pieces from £30*

Blue cardigan, midi dress & trainers

£190*

For cool days, about 5–12°C · Smart casual · 3 pieces from £30*

Blue cardigan, midi dress & brown shoes

£289*

For cool days, about 5–12°C · Smart casual · 3 pieces from £30*

Navy midi dress & trainers

£269*

For mild days, about 12–20°C · Outdoors · 2 pieces from £79*

Black midi dress & black penny loafers

£250*

For warm days, about 20–30°C · Smart casual · 2 pieces from £45*

Green jacket, black midi dress & olive mules

£520*

For mild days, about 12–20°C · Smart casual · 3 pieces from £160*

Brown midi dress & trainers

£175*

For mild days, about 12–20°C · Smart casual · 2 pieces from £50*

What to wear with a midi dress

With black · 44 looks

Cream cardigan, black midi dress & brown clogs

Midi dress, black trainers & burgundy bag

Black midi dress & Uggs

Burgundy midi dress & Uggs

Burgundy cardigan, black midi dress & Uggs

Brown jacket, blue midi dress & black trainers

With cream · 32 looks

Orange cardigan, brown midi dress & cream flats

Beige midi dress, trainers & red bag

Tan jacket, burgundy midi dress & flats

Beige midi dress, black adidas Campus & red bag

Cream cardigan, black midi dress & penny loafers

Striped gilet, floral midi dress & navy trainers

With red · 37 looks

Burgundy midi dress & Uggs

Burgundy midi dress, Uggs & brown bag

Burgundy cardigan, black midi dress & black ballet flats

Brown gilet, floral midi dress & black trainers

Burgundy coat, black midi dress & Uggs

Brown jacket, burgundy midi dress & Uggs

With brown · 29 looks

Brown gilet, white midi dress & pink trainers

Blue midi dress, brown clogs & brown bag

Blue midi dress & brown clogs

Brown jacket, blue midi dress & black ballet flats

Striped gilet, floral midi dress & brown boots

Jacket, striped midi dress & clogs

All looks

Red cardigan, beige midi dress & black trainers

Jacket, brown midi dress & adidas Spezials

Tan jacket, burgundy midi dress & black trainers

Green gilet, beige midi dress & trainers

Grey gilet, white midi dress & trainers

Black midi dress & trainers

Bomber jacket, midi dress & navy trainers

Midi dress & penny loafers

Blue cardigan, midi dress & trainers

Blue cardigan, midi dress & brown shoes

Navy midi dress & trainers

Black midi dress & black penny loafers

Green jacket, black midi dress & olive mules

Brown midi dress & trainers

What to wear with a midi dress

With black · 44 looks

Cream cardigan, black midi dress & brown clogs

Midi dress, black trainers & burgundy bag

Black midi dress & Uggs

Burgundy midi dress & Uggs

Burgundy cardigan, black midi dress & Uggs

Brown jacket, blue midi dress & black trainers

With cream · 32 looks

Orange cardigan, brown midi dress & cream flats

Beige midi dress, trainers & red bag

Tan jacket, burgundy midi dress & flats

Beige midi dress, black adidas Campus & red bag

Cream cardigan, black midi dress & penny loafers

Striped gilet, floral midi dress & navy trainers

With red · 37 looks

Burgundy midi dress & Uggs

Burgundy midi dress, Uggs & brown bag

Burgundy cardigan, black midi dress & black ballet flats

Brown gilet, floral midi dress & black trainers

Burgundy coat, black midi dress & Uggs

Brown jacket, burgundy midi dress & Uggs

With brown · 29 looks

Brown gilet, white midi dress & pink trainers

Blue midi dress, brown clogs & brown bag

Blue midi dress & brown clogs

Brown jacket, blue midi dress & black ballet flats

Striped gilet, floral midi dress & brown boots

Jacket, striped midi dress & clogs

All looks

Red cardigan, beige midi dress & black trainers

Jacket, brown midi dress & adidas Spezials

Tan jacket, burgundy midi dress & black trainers

Green gilet, beige midi dress & trainers

Grey gilet, white midi dress & trainers

Black midi dress & trainers