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.
-
These $50 Old Navy Zipped Boots Are Just as Chic as the $1500 Pair I Have Been Coveting Since Last WinterThey're on sale for $30 right now.
-
Looking Chic in Cropped Jeans This Winter Means Wearing This Boot Style and ColorElizabeth Olsen would know.
-
Sorry, Crewneck Tees—in 2026, Everyone With Taste Will Be Layering Sweaters Like ThisThe recipe for a perfect winter outfit.
-
My Sister Asked Me What She Should Buy From Amazon—30 Fashionable Items I SuggestedBasically, everything on my Black Friday wish list.
-
Elizabeth Olsen's The Row Boots Are Chic, But These Ones Cost $1360 LessIt's girl math.
-
The Ashley Olsen Way to Make Simple Black Coats Look Chic, Not BoringIt's so easy, yet so impactful.
-
This Once-Dated Legging Trend Is Getting Resurrected by Designers and the Fashion SetIt's baaack.
-
If You're Going to Wear This Controversial Legging Color Trend, This Is the Sneaker Color to Wear With ItIf you only wear black leggings, these may stun you.
