Summer is officially done, but don't cry because it's over. Think of all the amazing fall outfits you can dig out of your closet! One look I'm specifically thinking about is the ever-compatible dress-and-boots combo. You can still wear some of your summer dresses into the new season by pairing them with stylish boots, or it's a great excuse to buy a new fall dress. (You know you want to.) Either way, I rounded up 33 boots that will go with any mini, midi, or maxi dress your heart desires during these transitional temps and well into the chillier months ahead. From sophisticated knee-high boots to trendy Western-inspired ones, there's a pair here for everyone. And if you've never styled boots with a dress before, consider this your sign to try it before 2024 turns into 2025. Just think of how easy it will be to get ready in the morning.
If your dress has some fall florals on it, opt for some biker boots to add contrast. Or if you're going with a classic LBD, throw on a stiletto pair to elevate your whole ensemble. I spent hours browsing for the coolest pairs that will complement any dress you might grab for autumn, so keep scrolling to get inspired by the best in fall footwear. Thank me later.
These sold out so quickly last fall, and I have no doubt that the same will happen this season.
An exaggerated wide shaft makes a pair of black boots anything but boring.
The perfect partner for mini and midi dresses alike.
Your closet is missing these classic Frye moto boots with silver hardware. They'll last for ages, and the shaft also works for those with wider calves.
I'm a sucker for suede boots.
Sometimes the classics are the way to go.
Kitten-heel boots will make any dress look elevated and sleek.
Black leather and moto-style boots are an obvious pairing, but this chocolate suede is very compelling.
Consider a pair of off-white boots to stand out in a sea of black ones.
Sorry, just picking up my jaw because of how stunning this hue is.
Best paired with a prairie dress.
Introducing the perfect shade of brown for fall.
Burgundy is everywhere this season.
These are selling and selling fast.
These perfectly complement a midi dress.
Equestrian-inspired boots always look amazing with dresses.
A perfect everyday boot that works for you (and with all of your favorite dresses, not to mention skirts and leggings).
An absolutely elegant silhouette.
Don't let the suede fabric fool you; these are actually waterproof, so you'll get both fashion and function.
Just consider the endless styling opportunities.
Channel '90s Jennifer Aniston in a pair of slim-fitting stiletto boots. Nothing could be chicer.
If you want a subtler yeehaw vibe, these black Western boots are it.
Chelsea boots are a classic for a reason. Wear 'em with minis, midis, or maxis for an easy fall look.
Swap out your sneakers for these minimal flat boots instead.
Snakeskin boots are trending, and the stiletto heel is super sophisticated.
The higher, the better. These Chloé-inspired ones are stylish as can be.
Add some edge to your dress in the form of these square-toe moto boots.
Find me a better pair of boots. I'll wait.
According to Net-a-Porter, these are "trending now," and I can see why. I want to immediately pair them with a silk-chiffon boho dress.
Another Western pair, but this time subtler with a comfortable heel and on-trend coloring.
This beige shade will go with so many dresses in your closet, I'm sure.
The wider shaft and mid-calf height makes these perfect for wearing with flouncy silk and thicker knit dresses alike.
This croc-effect boot adds cool texture to any look.
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The Styling Tricks Defining Fall 2025 (and How to Pull Them Off IRL)The best part? You likely own almost everything you need.
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We Did the Research: These Are the 25 Best Pairs of Chelsea Boots, Hands DownThey're so back.
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Meghan Markle and Kate Middleton Agree: This Boot Trend Is Made for Skinny JeansAre you on the same page?
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Thanks, It's Madewell—32 Fall Finds I Almost Gatekept Just for MyselfA shopper's paradise.
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The Chicest People I Know Have a Thing for This Elegant Color PairingTime to try it this fall.
