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.

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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 MatchesFashion.com


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

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