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 fall ensembles with leggings. Well, two of the outfits featured in that piece showcase classic leggings with one of the most popular fall shoe trends. Yes, I’m referring to knee-high boots.
The choice may feel somewhat unexpected, with sneakers 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 favorite leggings.
Interested? Wonderful. Below, you’ll uncover a few standout looks showcasing how to wear knee-high boots and leggings, complete with shopping inspiration.
This is such a polished outfit choice with the relaxed blazer, chunky knit, leggings, and flat knee-high boots.
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.
For those chillier days later in fall and getting into winter, consider a white coat with your sweater, leggings, and boots. The belt around the sweater is also something to note here.
Here's another sleek legging outfit featuring the knee-high boots and sharp blazer.
Next, check out more stylish leggings.

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.
-
7 Expensive-Looking Outfits to Wear With Fall's Most Iconic Shoe Trend
Let your outfit do the talking.
-
Bella Hadid Wore the Season's It-Girl Legging Trend With the Flats Everyone Has Bought This Year
Summer 2025 summed up in one outfit.
-
Julia Garner Just Wore This Anti-Athleisure Shoe Trend With Leggings in NYC
I did not see this coming.
-
Forget Lace-Up Boots: This Casual and Easy Boot Trend Is About to Be Everywhere
Make this your first boot purchase for the season.
-
If You Want to Look as Elegant as Possible in Leggings and Pull-On Pants, Wear This Sweater Trend
As seen on Margot Robbie in West Hollywood.
-
It's Official: This Dated Legging Trend Is Back From the Dead
Elsa Hosk has spoken.
-
The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)
It's finally time to part ways with boring linen dresses.
-
I'm Manifesting a Fashionable Fall in NYC With These 36 Nordstrom Anniversary Sale Finds
Frye, AllSaints, Vince, Coach, and more.