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.

Pair The Printed Midi…
A patterned midi dress is one of our no-brainer go-to’s for transitional weather.

Zara Heart Print Midi Dress, $69.9, available at Zara

With A Slouch Boot
Change up your typical ankle boot for a suede over-the-knee boot with a bit of a slouch effect. The result? An elevated look that feels straight out of a fall campaign.

Sole Society Slouchy Tall Leather Boots , $152, available at QVC

Pair The Bold Mini…
A little animal print number just begs for a night out.

Ciao Lucia Victoria Dress, $295, available at Shop Super Street

With The Classic Black
If it ain’t broke, don’t fix it — and the minidress/over-the-knee boot situation is one that just works.

Gianvito Rossi Leather Over-The-Knee Slouchy Boots, $1975, available at Saks Fifth Avenue

Pair The Knit Dress…
The perfect fall dress looks a lot like this one. What’s better than a turtleneck-sweater-midi-dress hybrid?

Mango Turtleneck Dress, $119.99, available at Mango

With The Tight Boot
Like a pair of tights, but better.

Stuart Weitzman THE LOWLAND BOOT, $798, available at Stuart Weitzman

Pair The Dressy-Dress…
Your calendar full of almost -holiday-parties calls for textured fabric and seasonal tones.

Nina Ricci Frayed plissé silk dress, $1389, available at The Outnet

With The Platform
Balance out a fancier dress with a boot that has a bit of an edge. With a platform, you get the added height minus the skinny, wobbly heel.

Robert Clergerie Basilia Leather Over-the-Knee Wedge Platform Boots, $995, available at Bloomingdale’s

Pair The Post-Labor-Day White…
We’ve always liked being rule-breakers.

MiH Corduroy Dress, $295, available at

With A Pop Of Color
A neutral dress is the perfect opportunity to bring some color into the look, and a blush-y pink is a still-versatile change of pace from your usual black or brown.

L’Autre Chose Over The Knee Boots, $506.81, available at Farfetch

Like what you see? How about some more R29 goodness, right here?

29 New Takes On The Classic Black Bootie

Fast-Fashion Stores You Didn't Know You Can Buy Your Halloween Costume From

This Indie Designer Sale Is The Best Excuse To Overhaul Your Fall Closet