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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5 Street Style Trends from Milan Fashion Week That Will Be Everywhere This Fall -
Everyone in Paris Just Ditched Ankle Boots for This Boot Style That's Way More ElegantAnd super sleek.
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*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
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*Not* Ankle Boots—The Rich-Looking Shoe Trend That’s Quietly Taking Over for Fall 2025Shop the style inside.
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Black Boots Are Fine, But *This* Fall Shoe Color Trend Looks Rich as HellLily James is a fan.
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I Spent Over an Hour BrowsingReplica Store's New Arrivals—34 Standout Fall Finds I Can't Stop Thinking AboutYou'll want to see these.
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The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This FallIt's all about this styling trick.
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This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
