The Best Short, Midi, and Long Dresses to Wear With Boots This Fall

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


(Image credit: @raeannlangas)

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


(Image credit: @greceghanem)

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


(Image credit: @babba)

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.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.