How To Wear This Tricky Outfit Combination All Fall Long

When it comes to building an outfit, some proportions and pairings just make sense. Take a high-waisted pant and a crop top, for example: one picks up where the last left off. Or, think about a midi dress and ankle boots — what's not to love about that perfect sliver of exposed lower leg?
But when it comes to over-the-knee boots, you may feel like you're restricted to micro-mini skirts, short-suits, or oversized sweatshirts (sans pants) because you've gotta show off your shoes. Right? Well, not always. Since last fall, we've been seeing taller boots get paired with longer dresses, offering a look that feels as rooted in Bohemia as it is modern. And it's not as much replacing the whole lampshading thing as it's offering up a solid alternative for people who don't want to dress like Ariana Grande.
Since dresses + boots = one of the best outfit formulas fall has to offer, you may as well get a few of the styling options down pat. Because whether you pair your over-the-knee boots with a party-ready mini or a printed prairie dress, you'll no doubt get some significant mileage out of them this season. Here's just a few to wear this sometimes-tricky, but always worth it, fall style combination.
At Refinery29, we’re here to help you navigate this overwhelming world of stuff. All of our market picks are independently selected and curated by the editorial team. If you buy something we link to on our site, Refinery29 may earn commission.

More from Shopping

R29 Original Series