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.
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If Reading Brontë in Central Park is Your Vibe, Then You’re Going to Love These 28 Fall Sweaters from Gap, Old Navy, and Banana RepublicStriped sweaters and cashmere.
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Wait, J.Crew is 30%-Off Sitewide Right Now—These Are the Chic Fall Pieces in My CartThe fall 2025 collection is so good.
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Fashion People in Paris, Copenhagen, and NYC Are Hinting at the Styling Hack They'll Be Using All Fall 2025It's easy yet impactful.
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Shopbop Lovers to the Front—These 40 Styles Are Going to Be Huge This FallGive your wardrobe a fall facelift.
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This Just In: The Denim Wash That's About to Dominate Every Cool Outfit This FallWill you love it or hate it?
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My Mom Only Shops at T.J. Maxx and Marshalls—Here's What She Sent Me to Buy for Fall 2025She had me at under-$100 Uggs and Levi's.
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52 Elegant Fall Fashion Finds That Whisper Wealth But Don't Top $250Money talks.
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Found: The Perfect Finishing Touch to Your Elegant and Sophisticated Fall OutfitsHint: It's not a handbag.
