21 Chic, Autumn-Ready Midi Dresses That Make Getting Dressed So Easy
Autumn is on the horizon, making now the perfect time to find your dream autumn midi dress.
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.
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.
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.
Shop the Best Autumn Midi Dresses:
This post was originally published at an earlier time and has since been updated.

Elinor Block was one of the earliest team members of Who What Wear UK, starting her tenure working across both Who What Wear and Byrdie, which were owned by the original parent company, Clique, at the time. Her specialism in fashion and beauty established her multifaceted role as Assistant Editor, which she developed over six years from 2016 to 2022 to become Deputy Editor. She is now the Head of Editorial at fashion tech company Drest.
-
Coniglio Palm Beach Just Launched at Shopbop—Consider These Vacation-Ready Pieces for Your Next GetawayYour wardrobe for your next tropical stay is here.
-
Yes, Cyber Month Is Over, But Nordstrom Just Dropped Some Sneaky New Markdowns—These 16 Are BestShop these surprise deep discounts ahead of the holidays.
-
Suddenly, This Revealing Dress Trend Is Popular Again—These Are the Shoes That Make It Look TastefulJ.Lo knows how to dress both sophisticated and sultry.
-
3 Winter Trends That Were Practically Invented With the Gen Z Fashion Crowd in MindIt's all for the cool kids.
-
It's Here: Our Fancy Winter Dress EditConsider your holiday plans covered.
-
This Is the It-Girl Way to Wear a Fancy Dress During the DayIt's so easy and chic.
-
Leslie Bibb Just Wore the Fall 2025 Version of a Classic ShirtdressShe knows what's popular.
-
How to Make a Boring Sweater Look Cooler: Buy This Pretty Under-$40 Accessories TrendOn to more interesting outfits.
-
Of All the Dôen Dresses, These 21 Are the Most Likely to Go Viral and Sell OutBRB—building my dream dress wardrobe.
-
Suddenly, Everyone With Great Taste Is Styling These 7 "Dated" Fall Dress TrendsA 2017 throwback and a Victorian vibe shift.