This Popular Shoe Trend Looks So Chic With Classic Leggings

Leggings are a staple in the wardrobes of many. In fact, we recently showcased a range of stylish winter ensembles with leggings. Well, one of the outfits featured in that piece showcase classic leggings with one of the most popular winter shoe trends. Yes, I’m referring to knee-high boots.
The choice may feel somewhat unexpected, with trainers or slides often being the go-tos, but knee-high boots (both flat and heeled) actually work quite well with classic black leggings. The shoe silhouette is certainly a way to instantly dress up your favourite leggings.
Interested? Wonderful. Below, you’ll uncover a few standout looks showcasing how to wear knee-high boots and leggings, complete with shopping inspiration.
Knee-High Boots and Leggings Outfits to Try
Look 1
This is such a polished outfit choice with the relaxed blazer, chunky knit, leggings, and flat knee-high boots.
SHOP THE LOOK:
Look 2
A longline coat will make any ensemble feel all the chicer. This look is quite cool with the sweatshirt and leggings teamed with unexpected heeled boots.
SHOP THE LOOK:
Look 3
For those chillier winter days, consider a white coat with your knitwear, leggings, and boots. The belt around the jumper is also something to note here.
SHOP THE LOOK:
Look 4
Here's another sleek legging outfit featuring the knee-high boots and sharp blazer.
SHOP THE LOOK:
Next Up, The WWW Gift Guide: 58 Chic Buys We'd Love to Open Ourselves
This post originally appeared on Who What Wear US.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
8 Classic Outfits to Try This Summer If You're a French Girl at Heart (Like Me)
Chic.
-
Stop With the Ankle Boots—Miniskirts Should Only Be Worn Like *This* in 2025
Period.
-
Spotted in Los Angeles: The Coolest Shoes to Wear With Denim Shorts This Season
Denim shorts never looked so good.
-
Is It Just Me, or Are Fashion People Everywhere Skipping Sandals for This Cooler Year-Round Silhouette?
These boots were made for walking.
-
Step Away From the Black Leggings—This Is the Low-Key Legging Colour Trend You'll See Everywhere This Summer
Jennifer Lopez-approved.
-
Summer Is Here! 4 Fun and Incredibly Chic Colour Combinations I've Spotted Fashion People Wearing
Perfect pairings.
-
See Ya Later, Black Leggings—J.Lo Just Wore a Very Summery Colour With Trainers Instead
The easiest upgrade.
-
I'm Heading to the South of France—15 Outfits I'm Re-Creating to Look Like a Local
Euro summer loading…