32 Elegant Dresses to Wear With Boots This Fall | Who What Wear

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I feel like every season has a signature outfit formula, and for fall, mine is a dress and boots. Both elements get annual updates based on current trends, but it's an outfit combination I always revert back to. The moment the calendar strikes October, I get hyperfixated on my favorite fall boots and dresses, and my other clothes take a back seat. Whether it's a mini, midi, or maxi, I think adding a pair of sleek knee-high boots creates the perfect fall outfit.

Since 2024 has been the year of elegance, the fall dresses I'm reaching for this season are full of sophisticated touches—from draped details to shoulder-baring silhouettes and full skirts. I took a scan through my favorite retailers in search of elevated fall dresses to add to my wardrobe and found 32 utterly chic options that are too good not to share. Below, I'm highlighting the best elegant dresses to wear with boots.

That slit shows off a pair of boots perfectly.

One word: chic.

Imagine this print juxtaposed with sleek leather boots.

I would style this maxi exactly like that.

I can't resist draping details.

Look at those shoulder details.

Pair with boots in the fall and flats in the spring.

There's a reason this one is always sold out.

This neckline is so pretty.

Just add black boots.

The color of the season.

For the office.

That's one versatile dress.

I'm taking styling notes.

This color screams fall.

Made for tights and boots.

How elegant.

Timeless with a twist.

It's the tie detail for me.

Dôen never misses.

The perfect under-$100 fall dress.

The collar!

You can just tell this is cozy.

Simple and sophisticated.

Such a good mini.

Chocolate brown always looks elevated.

This dress looks significantly more expensive than it is.

I didn't know I needed a denim maxi dress until now.

I just love the pleating details.

A very chic mix of polka dots and lace.

It's tweed season.

The fall version of the LBD.

Dress for yourself.

By Kristen Nichols

She can do anything.

By Eliza Huber

A combo I will live in.

By Nikki Chwatt

The perfect alternative.

By Eliza Huber

Fashion person–approved buys ahead.

By Chichi Offor

There's something for every budget.

By Judith Jones

Discounted gems from Nordstrom, Zara, J.Crew, and more.

By Jennifer Camp Forbes

From classic to quirky.

By Natalie Cantell

These cool-girl picks are bound to sell out fast.

By Jennifer Camp Forbes

Buh-bye, jeans.

By Nikki Chwatt