Fact: The easiest, most timeless fall outfit on the planet is a dress and boots. It's comfortable, appropriate for just about any occasion, and it takes zero time and effort to put together. It takes even less time if you have several dresses and boots to choose from, and now just happens to be the best time to shop for fall dresses, as the stores are stocked. But where to even begin? I'm here to help with that.
For this fun shopping activity, I broke things down into three dress styles which I paired with the best boot style to wear with each. We have minidresses with knee boots, midi dresses with lug-sole boots, and maxi dresses with kitten-heel ankle boots. Below, I found some of the best styles from each category for you to mix and match to your heart's desire. Prepare to feast your eyes on dresses from the likes of Zara, Reformation, and Nordstrom, and boots by the likes of The Row, Sam Edelman, and Mango (to name a few).
Minidresses + Knee Boots
When it comes to wearing minidresses in the fall, it's all about balancing proportions. Knee boots do just that. Not only do they look cool, but they also keep your legs warm(ish).
Shop Minidresses
Shop Knee-High Boots
Midi Dresses + Lug-Sole Boots
People wear lug-sole boots with everything these days, but fashion people really love wearing them with midi dresses in the fall. They make almost any midi dress look cooler.
Shop Midi Dresses
Shop Lug-Sole Boots
Long Dresses + Kitten-Heel Ankle Boots
Long dresses are, well, long, so wanting to add a bit of height so they don't drag on the floor is valid. The best way to do so is with a pair of kitten heel ankle boots. That way, you get both comfort and height and you'll look very chic while you're at it.
Shop Long Dresses
Shop Kitten-Heel Ankle Boots
Next up, 27 trendy boots that are anything but boring.
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I Walk Over 5 Miles a Day Working in Manhattan—Here's an Editor-Approved City Girl's Guide to Fall ShoesPlus, how I'd style them.
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Forget What You've Heard—Ankle Boots Are Still In, and This Expensive-Looking (But Just $50) Pair Is ProofGrab them before they're gone.
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Wearing a Preppy Cardigan With This Controversial Boot Trend Makes It Look 10x CoolerYou won't believe it.
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I'm Building the Boho-Chic Closet of My Dreams—31 Fall Finds From Free People and Anthropologie That Fit the BillLet's talk about micro shorts and Western boots.
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Jeans, Who? It Girls Everywhere Are Wearing Boots With This Anti-Denim Trend Right NowIt will also be a fashion person's go-to uniform this winter, too.
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This "Ugly" Shoe Trend Is Officially Back From 2016—But This Time, It's BetterSpotted in London and NYC.
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This Is the 2025 Way to Wear the Ankle Boot Trend Everyone Bought 4 Years AgoPSA: Don't toss them yet!
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Move Over, Jeans—The Chicest People I Know Are Wearing This Expensive-Looking Pant Trend With BootsSpotted on Naomi Watts.
