Women's outfits with knee-high boots

Knee-high boot outfits with skirts, dresses, jeans and leggings, for fall and winter. 69 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

What goes with knee-high boots

On top: Knitwear or t-shirts & tops
Bottoms: Skirts or pants
Layers: Cardigans or jackets
Colors that work: Black, brown, cream and white

Get looks picked for you · 1-minute quiz

With black · 50 looks

Midi dress, yellow knee-high boots & black bag
$335
For mild days, about 55–70°F · Smart casual · 3 pieces from $110
Beige trench coat, black maxi dress & yellow knee-high boots
$330
For cool days, about 40–55°F · Work · 3 pieces from $100
Black dress, black knee-high boots & pink bag
$285
For mild days, about 55–70°F · Smart casual · 3 pieces from $90
Brown cardigan, red maxi dress & black knee-high boots
$246
For mild days, about 55–70°F · Smart casual · 3 pieces from $56
White sweater, white skirt & black knee-high boots
$240
For cool days, about 40–55°F · Date night · 3 pieces from $50
Olive dress, black knee-high boots & olive bag
$407
For mild days, about 55–70°F · Smart casual · 3 pieces from $78

With brown · 37 looks

With white · 15 looks

With cream · 16 looks

All looks

69 looks

Pink top, white jeans & brown knee-high boots

$269

For cool days, about 40–55°F · Weekend · 3 pieces from $64

Would you wear it?

Plaid shirt, pants & black knee-high boots

$350

For mild days, about 55–70°F · Smart casual · 3 pieces from $83

Would you wear it?

Beige sweater, blue jeans & yellow knee-high boots

$340

For cool days, about 40–55°F · Everyday · 4 pieces from $80

Would you wear it?

Yellow cardigan, grey sweater & white wide-leg pants

$315

For cool days, about 40–55°F · Smart casual · 4 pieces from $60

Would you wear it?

White sweater, pink pants & brown suede boots

$305

For cool days, about 40–55°F · Smart casual · 4 pieces from $50

Black maxi dress, brown suede boots & beige bag

$265

For mild days, about 55–70°F · Date night · 3 pieces from $85

Trench coat, blue sweater & brown pleated pants

$673

For cool days, about 40–55°F · Smart casual · 4 pieces from $98

Green cardigan, turtleneck & midi skirt

$946

For cool days, about 40–55°F · Smart casual · 4 pieces from $148

Jacket, white oxford shirt & jeans

$973

For cold days, about 25–40°F · Everyday · 5 pieces from $140

Black jacket, striped sweater & midi skirt

$976

For cool days, about 40–55°F · Smart casual · 4 pieces from $148

Grey rugby shirt, wide-leg pants & burgundy knee-high boots

$536

For cool days, about 40–55°F · Smart casual · 3 pieces from $140

Purple cardigan, dress & black knee-high boots

$396

For mild days, about 55–70°F · Smart casual · 3 pieces from $108

Green dress & brown knee-high boots

$207

For mild days, about 55–70°F · Smart casual · 2 pieces from $47

Tee, orange pants & brown knee-high boots

$786

For mild days, about 55–70°F · Everyday · 4 pieces from $85

Green jacket, black tee & black skirt

$854

For mild days, about 55–70°F · Everyday · 4 pieces from $88

Brown jacket, brown dress & yellow knee-high boots

$796

For mild days, about 55–70°F · Smart casual · 3 pieces from $118

Brown jacket, polka-dot dress & brown knee-high boots

$834

For mild days, about 55–70°F · Smart casual · 3 pieces from $168

Plaid cardigan, black midi dress & black knee-high boots

$806

For mild days, about 55–70°F · Smart casual · 3 pieces from $150

How to wear knee-high boots

Counted from 42 of these looks.

What goes with knee-high boots

On top: Knitwear or t-shirts & tops
Bottoms: Skirts or pants
Layers: Cardigans or jackets

Colors that work

Black, brown, cream and white 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 $315 and $786; the typical one is $396. 16 include a piece on sale. Swap any piece to change the total.

Brands in these looks

Most pieces come from Nine West, White Fox, Lisa Says Gah, Oak + Fort and tentree. Each look checks out on the stores' own sites, one store at a time.

Women's outfits with knee-high boots

What goes with knee-high boots

With black · 50 looks

Midi dress, yellow knee-high boots & black bag

Beige trench coat, black maxi dress & yellow knee-high boots

Black dress, black knee-high boots & pink bag

Brown cardigan, red maxi dress & black knee-high boots

White sweater, white skirt & black knee-high boots

Olive dress, black knee-high boots & olive bag

With brown · 37 looks

Brown sweater, pink pants & brown suede boots

Beige trench coat, brown maxi dress & brown suede boots

Red sweater, brown midi skirt & yellow knee-high boots

Brown midi dress, yellow knee-high boots & brown bag

Yellow cardigan, brown sweater & brown midi skirt

Green turtleneck, black skirt & brown knee-high boots

With white · 15 looks

Striped polo, black leggings & black knee-high boots

Striped polo, grey leggings & black knee-high boots

White jacket, pink sweater & black skirt

Black jacket, white turtleneck & olive wide-leg pants

Jacket, black turtleneck & purple jeans

Black jacket, white sweater & brown leggings

With cream · 16 looks

Beige cardigan, pink sweater & midi skirt

Cream cardigan, blue sweater & cream pants

Khaki puffer jacket, charcoal top & brown jeans

Coat, blue sweater & taupe skirt

Cardigan, turtleneck & pants

Black wool coat, knit polo & khaki pleated pants

All looks

Pink top, white jeans & brown knee-high boots

Plaid shirt, pants & black knee-high boots

Beige sweater, blue jeans & yellow knee-high boots

Yellow cardigan, grey sweater & white wide-leg pants

White sweater, pink pants & brown suede boots

Black maxi dress, brown suede boots & beige bag

Trench coat, blue sweater & brown pleated pants

Green cardigan, turtleneck & midi skirt

Jacket, white oxford shirt & jeans

Black jacket, striped sweater & midi skirt

Grey rugby shirt, wide-leg pants & burgundy knee-high boots

Purple cardigan, dress & black knee-high boots

Green dress & brown knee-high boots

Tee, orange pants & brown knee-high boots

Green jacket, black tee & black skirt

Brown jacket, brown dress & yellow knee-high boots

Brown jacket, polka-dot dress & brown knee-high boots

Plaid cardigan, black midi dress & black knee-high boots

How to wear knee-high boots

What goes with knee-high boots

Colors that work

What a complete look costs

Brands in these looks

Women's outfits with knee-high boots

What goes with knee-high boots

With black · 50 looks

Midi dress, yellow knee-high boots & black bag

Beige trench coat, black maxi dress & yellow knee-high boots

Black dress, black knee-high boots & pink bag

Brown cardigan, red maxi dress & black knee-high boots

White sweater, white skirt & black knee-high boots

Olive dress, black knee-high boots & olive bag

With brown · 37 looks

Brown sweater, pink pants & brown suede boots

Beige trench coat, brown maxi dress & brown suede boots

Red sweater, brown midi skirt & yellow knee-high boots

Brown midi dress, yellow knee-high boots & brown bag

Yellow cardigan, brown sweater & brown midi skirt

Green turtleneck, black skirt & brown knee-high boots

With white · 15 looks

Striped polo, black leggings & black knee-high boots

Striped polo, grey leggings & black knee-high boots

White jacket, pink sweater & black skirt

Black jacket, white turtleneck & olive wide-leg pants

Jacket, black turtleneck & purple jeans

Black jacket, white sweater & brown leggings

With cream · 16 looks

Beige cardigan, pink sweater & midi skirt

Cream cardigan, blue sweater & cream pants