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



This comfortable, minimalist look is just right for 2020.

Stompy ankle boots make a shirtdress so much cooler.



This high-fashion combination speaks for itself.



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



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

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



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

H&M and I are clearly on the same page with this outfit.

Zara made a dress version of the season's biggest sweater trend (collared), and it's great.

Mini dresses are my favorite for wearing with stompy boots, and this one is just right.

The faux leather collar makes this stand out.

I love a brocade dress this time of year.

This is going to sell out, so you know what to do.

This is basically as comfortable as a blanket.

I love every iteration of this Ciao Lucia dress.

I predict that lots of fashion people have already ordered this dress.

Pretty much any dress Ganni makes will look cool with boots.

Shop Boots to Wear With the Dresses

638 Nordstrom shoppers are viewing these boots right now.

Get ready to see these all over your Instagram feed.

These also come in brown croc and black.

Good luck finding a cooler pair of boots for this price.

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