5 Stylish Ways to Wear Over-the-Knee Boots This Fall

By Meghan Blalock

There are fall trends that come and go, and then there are fall trends that prove the test of time. We’ve already seen that blazers are one of those perennially stylish pieces that you can wear year after year—and over-the-knee boots are another.

Celebrity stylists Emily Current and Meritt Elliott know this better than anyone, and when one of you, our dear readers, asked for advice on how to wear the trend this season, they heeded the call.

Keep scrolling for their advice on how to wear over-the-knee boots this fall!

1. With tea-length, ’70s-inspired dresses

French Connection Long Sleeved Tea Dress

A mix of sweet and edgy, this is certainly a bold look but it’s a fun one if you can pull it off!

Free People Charlotte Midi Dress

Related: 13 Fall Dresses Perfect for Under Your Coat

2. With skinny trousers and an oversized chunky knit sweater

Helmut Lang Oversize Honeycomb Mesh Sweater

Try these in classic fall colors for a major impact.

J. Crew Maddie Pant in Pinstripe

Related: 9 of the Most Stylish Black Trousers for Fall

3. With a pleated skirt and crew-neck sweater

& Other Stories Cashmere Sweater

This look will give you a delightfully ’70s prep vibe.

Zara Pleated Short Skirt

Related: 22 Fall Outfit Ideas Built Around Our Favorite Skirts

4. With leggings and a preppy top

Zara Zip Leggings

T by Alexander Wang Ribbed Knit Leggings

Related: Dress up Your Casual Pieces With These 10 Easy Tips

5. With an oversized t-shirt, a shrunken blazer, and skinny jeans

Elizabeth & James Ramsay Stretch Twill Blazer

This will look equal parts casual and sleek.

ASOS Rib Short Sleeve Top

Related: 14 Sleek Blazers to Look Put Together Instantly

Shop some of our favorite over-the-knee boots right now!

Zara Long Leather Boot

Manolo Blahnik Pascalarehi Over-The-Knee Boots

Stuart Weitzman The 5050 Boot

Nicholas Kirkwood Suede Block Heel Over the Knee Boots

More From Who What Wear:
Thigh-High Boots: A Beginner’s Guide
Your Complete Guide To Wearing Prints This Fall
Why Everyone Will Be Wearing Butterflies This Fall