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.
-
Not Black, Not Brown: The 2026 Boot Color Trend That Makes Every Outfit ElegantJust like that.
-
Winter's Just Around the Corner—13 Standout Zara Finds I Predict Will Sell Out Before the End of the MonthAffordable funnel-neck jackets, argyle knits, and rich-looking flats inside.
-
My Stylish 56-Year-Old Mom Is a Picky Shopper—31 Chic Under-$100 Nordstrom Finds She Approves OfFunnel-neck coats, Fair Isle knits, and Levi's jeans inside.
-
If Chic Jeans-and-Boots Outfits Are the Goal, Don't Miss These Standout Picks From Zara, Madewell, and NordstromBring on a stylish fall-and-winter closet.
-
My Honest Take on the Winter It Boots Every Fashion Person Is Talking AboutFrom Khaite to Free People.
-
Just so You Know, Zara Already Has All the Best Shoes for Winter 2025Shop before they sell out.
-
Of All Her Outfits, *This* Hailey Bieber Look Is Stuck in My BrainAnd I will be re-creating it.
-
Cool Sneakers, Flats, and Boots Are the Vibe—These 36 Styles Are Heavily Discounted for Cyber MondayEverything from Khaite to Ref to Adidas is at least 25% off.
