What to wear with knee-high boots

Knee-high boot outfits with skirts, dresses, jeans and leggings, for autumn and winter. 82 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

With black · 53 looks

Black puffer jacket, cream sweatshirt & grey joggers
£294*
For cold days, about −5 to 5°C · Active · 5 pieces from £42*
Black gilet, cream quarter zip & cream joggers
£196*
For cool days, about 5–12°C · Active · 4 pieces from £38*
Brown gilet, black quarter zip & green joggers
£196*
For cool days, about 5–12°C · Active · 4 pieces from £38*
Brown top, black jeans & olive knee-high boots
£278*
For mild days, about 12–20°C · Weekend · 3 pieces from £87*
Black puffer jacket, brown quarter zip & grey joggers
£241*
For cold days, about −5 to 5°C · Active · 4 pieces from £38*
Green tee, joggers & black knee-high boots
£307*
For mild days, about 12–20°C · Active · 3 pieces from £94*

With green · 23 looks

With brown · 37 looks

With grey · 20 looks

All looks

82 looks

Purple jumper, cream trousers & black knee-high boots

£275*

For cool days, about 5–12°C · Smart casual · 3 pieces from £60*

Would you wear it?

Black puffer jacket, green tee & joggers

£295*

For cold days, about −5 to 5°C · Active · 4 pieces from £45*

Would you wear it?

Dress & black knee-high boots

£174*

For mild days, about 12–20°C · Outdoors · 2 pieces from £55*

Would you wear it?

Black jacket, grey hoodie & green joggers

£295*

For cool days, about 5–12°C · Active · 4 pieces from £65*

Would you wear it?

Black joggers, red knee-high boots & black bag

£189*

For warm days, about 20–30°C · Active · 4 pieces from £42*

Orange fleece, navy tee & navy trousers

£297*

For cool days, about 5–12°C · Outdoors · 5 pieces from £60*

Blue Carhartt jacket, sweatshirt & joggers

£659*

For cool days, about 5–12°C · Active · 5 pieces from £70*

Navy overshirt, green tee & navy trousers

£354*

For mild days, about 12–20°C · Everyday · 4 pieces from £55*

Brown fleece, hoodie & jeans

£436*

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

Olive bomber jacket, brown sweatshirt & navy trousers

£706*

For mild days, about 12–20°C · Outdoors · 4 pieces from £106*

Navy jacket, green sweatshirt & joggers

£611*

For cool days, about 5–12°C · Active · 5 pieces from £70*

Striped coat, cream jumper & black trousers

£539*

For cold days, about −5 to 5°C · Smart casual · 4 pieces from £110*

Brown jacket, blue fleece & brown joggers

£541*

For cold days, about −5 to 5°C · Active · 4 pieces from £85*

Jacket, olive tee & brown trousers

£560*

For mild days, about 12–20°C · Everyday · 5 pieces from £55*

Black jacket, black jumper & corduroy trousers

£671*

For cool days, about 5–12°C · Outdoors · 4 pieces from £111*

Black overshirt, striped top & cream trousers

£540*

For cool days, about 5–12°C · Everyday · 4 pieces from £65*

Orange jumper, brown trousers & black knee-high boots

£389*

For cool days, about 5–12°C · Smart casual · 3 pieces from £105*

Cream gilet, cream maxi dress & black knee-high boots

£226*

For mild days, about 12–20°C · Everyday · 3 pieces from £30*

What to wear with knee-high boots

With black · 53 looks

Black puffer jacket, cream sweatshirt & grey joggers

Black gilet, cream quarter zip & cream joggers

Brown gilet, black quarter zip & green joggers

Brown top, black jeans & olive knee-high boots

Black puffer jacket, brown quarter zip & grey joggers

Green tee, joggers & black knee-high boots

With green · 23 looks

Brown jacket, jumper & cream trousers

Brown trench coat, roll neck & green trousers

Green tee, charcoal jeans & black knee-high boots

Tee, navy joggers & olive knee-high boots

Charcoal gilet, olive top & charcoal trousers

Cream sweatshirt, grey joggers & olive knee-high boots

With brown · 37 looks

Brown puffer jacket, cream quarter zip & navy joggers

Brown hoodie, black trousers & olive knee-high boots

Brown puffer jacket, cream sweatshirt & grey joggers

Brown puffer jacket, black jumper & white trousers

Brown top, navy shorts & black knee-high boots

Brown puffer jacket, cream sweatshirt & grey joggers

With grey · 20 looks

Floral dress, black knee-high boots & bag

White top, joggers & red knee-high boots

Grey tee, grey joggers & olive knee-high boots

Red jacket, grey jumper & cream trousers

Tee, grey joggers & olive knee-high boots

Grey hoodie, black trousers & olive knee-high boots

All looks

Purple jumper, cream trousers & black knee-high boots

Black puffer jacket, green tee & joggers

Dress & black knee-high boots

Black jacket, grey hoodie & green joggers

Black joggers, red knee-high boots & black bag

Orange fleece, navy tee & navy trousers

Blue Carhartt jacket, sweatshirt & joggers

Navy overshirt, green tee & navy trousers

Brown fleece, hoodie & jeans

Olive bomber jacket, brown sweatshirt & navy trousers

Navy jacket, green sweatshirt & joggers

Striped coat, cream jumper & black trousers

Brown jacket, blue fleece & brown joggers

Jacket, olive tee & brown trousers

Black jacket, black jumper & corduroy trousers

Black overshirt, striped top & cream trousers

Orange jumper, brown trousers & black knee-high boots

Cream gilet, cream maxi dress & black knee-high boots

What to wear with knee-high boots

With black · 53 looks

Black puffer jacket, cream sweatshirt & grey joggers

Black gilet, cream quarter zip & cream joggers

Brown gilet, black quarter zip & green joggers

Brown top, black jeans & olive knee-high boots

Black puffer jacket, brown quarter zip & grey joggers

Green tee, joggers & black knee-high boots

With green · 23 looks

Brown jacket, jumper & cream trousers

Brown trench coat, roll neck & green trousers

Green tee, charcoal jeans & black knee-high boots

Tee, navy joggers & olive knee-high boots

Charcoal gilet, olive top & charcoal trousers

Cream sweatshirt, grey joggers & olive knee-high boots

With brown · 37 looks

Brown puffer jacket, cream quarter zip & navy joggers

Brown hoodie, black trousers & olive knee-high boots

Brown puffer jacket, cream sweatshirt & grey joggers

Brown puffer jacket, black jumper & white trousers

Brown top, navy shorts & black knee-high boots

Brown puffer jacket, cream sweatshirt & grey joggers

With grey · 20 looks

Floral dress, black knee-high boots & bag

White top, joggers & red knee-high boots

Grey tee, grey joggers & olive knee-high boots

Red jacket, grey jumper & cream trousers

Tee, grey joggers & olive knee-high boots

Grey hoodie, black trousers & olive knee-high boots

All looks

Purple jumper, cream trousers & black knee-high boots

Black puffer jacket, green tee & joggers