18 Chic, Autumn-Ready Midi Dresses That Make Getting Dressed So Easy

I don’t have a fashion crystal ball, sadly, so I can’t tell you what the weather will be in a few weeks’ time. But you know what I can tell you? As of right now the leaves are turning brown indicating autumn is here, and that, my friends, is what I like to call midi-dress time. For starters, it’s the best length whatever your height. It’s also great for the slightly warmer autumn days but also a great option for cooler months, making it the ideal outfit option for the changeable weather we’re currently experiencing. What I’m saying is, and there’s no fighting me on this, the midi dress reigns supreme. Hands down, it’s also the best frock to wear with boots.


(Image credit: @annacascarina


Anna wears a black midi dress with knee-high boots and a fringed jacket.

In short, it is the Goldilocks of dresses—not too long and not too short, which makes it ideal for showing off your footwear. For this coming season, there are quite a few ankle-boot trends that are bubbling up, and let me tell you, you don’t want to be hiding your fancy new shoes under too much material.


(Image credit: @styleidealist)

Karina wears a printed midi dress with cowboy boots and a maxi coat.

So without any more faffing, here is my list of the best autumn midi dresses you’re going to love wearing with boots—or any footwear for that matter


(Image credit: @thandimaq)

Thandi wears a bright midi dress with platftorm ankle boots.


Next Up: The 9 New-In Pieces I'm Adding to My Wish List This Week

This post was originally published at an earlier time and has since been updated.

Opening image: @styleidealist

Elinor Block