13 Fall Dresses to Wear With 2020's Biggest Shoe Trend

Before I inevitably resign myself to a winter filled with sweatpants and jeans, I've been seizing this mild-temperature moment and am wearing dresses as much as possible before it turns frigid. There are a lot of cute fall dresses out there, but the way to take them from cute to cool this season is with a certain shoe trend.

You've probably heard and/or noticed by now that chunk Chelsea boots are fall 2020's #1 shoe trend by a mile. These stompy boots easily toughen up anything they're paired with but especially dresses. Whether you go for an ankle or knee-high pair (depending on the dress) of lug-sole Chelsea boots, you will instantly look like you know what you're doing.

This shoe trend is surprisingly versatile, but if you want to get specific, the best types of dresses to choose are casual mini dresses, sweater and knit dresses, and relaxed-fitting midi dresses. To get you started, I found 13 stylish fall dresses that would look perfect with chunky Chelsea boots, along with a few of my favorite pairs of boots and some styling inspiration via Instagram. Scroll for your new favorite two-piece outfit.

See the Styling Inspiration


(Image credit: @smythsisters)

This comfortable, minimalist look is just right for 2020.


(Image credit: @champagnemani)

Stompy ankle boots make a shirtdress so much cooler.


(Image credit: @greceghanem)

This high-fashion combination speaks for itself.


(Image credit: @chrissyford)

Forget heels—this is the shoe trend to wear with a mini.


(Image credit: @eggcanvas)

Make any dress instantly more casual by adding an oversized sweatshirt and Chelsea boots.


(Image credit: @_jeanettemadsen_


We love the way this fancy high-slit dress contrasts with the rugged boots.


(Image credit: @yoyokulala)

While this dress would work well with any shoe style, every cool girl I know of would choose to toughen it up with the boots.

Shop Dresses

Shop Boots to Wear With the Dresses

Next up, 12 fresh ways to wear dresses with boots this fall.

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.