How to Wear Ankle Boots
with Leggings

Just because leggings are considered a wardrobe staple that doesn’t mean we always know exactly how to style then.

Here, 8 outfit ideas that highlight exactly how to wear ankle boots with leggings.

SHOW SOME
ANKLE WITH
LOW-CUT BOOTIES

Wearing an extra-long pair of leggings or tall socks with such a low-cut shoe throws off your proportions in an unflattering manner. 

BRIGHTON THE DAY

1

LET YOUR SOCKS PEEK OUT ABOVE YOUR LACE-UP BOOTS

Hiking & combat boots with just an inch or two of socks sticking out from the top gives off a supremely autumnal vibe.

EDWARD BERTHELOT

2

AVOID BUNCHING AT THE ANKLES

Tuck your lengthy leggings into a pair of slightly taller boots, or roll up the hem, so they fit just right. 

MELODIE JENG

3

PAIR DETAILED BOOTIES WITH SIMPLE LEGGINGS…AND VICE VERSA

The best way to give your boots space to shine? Stick to good old-fashioned black cotton leggings. 

EDWARD BERTHELOT

4

EMBRACE COLORS AND TEXTURES

Try to stick to classic black or dark brown footwear, to give your funky leggings a solid base. 

SAV/
CONTRIBUTOR

5

THE SHORTER THE HEEL, THE SHORTER YOUR TOP CAN BE

High heels (3" & up) look better with a long shirt while low heels work best with shorter tops. It all comes down to proportions.

EDWARD BERTHELOT

6

ADD AN OVERSIZE SWEATER OVER YOUR WORKOUT GEAR

Our tip for heading to brunch in yoga pants and your cute new booties? Be sure to add a thigh-grazing knit into the mix. 

MARK NOLAN/
STRINGER

7

WHEN IN DOUBT, STICK WITH THE CLASSICS

Black leggings & black booties will always look cool together, especially when worn with an oversize button down or chunky knit…or both.

MARC PIASECKI

8

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