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.
LIONESS
Original Sin Midi Dress
That slit shows off a pair of boots perfectly.
Helsa
The Little Lady Dress
DÔEN
Bijou Shirred Floral-Print Organic Cotton-Voile Midi Dress
Imagine this print juxtaposed with sleek leather boots.
Camila Coelho
Lucia Maxi Dress
I would style this maxi exactly like that.
I can’t resist draping details.
Cult Gaia
Alyssa Knit Dress
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.
NA-KD
Soft Line Midi Dress
This neckline is so pretty.
Camila Coelho
Olesya Mini Dress
L’Academie by Marianna
Belmore Midi Dress
That’s one versatile dress.
Reformation
Holland Cashmere Turtleneck Sweater Dress
I’m taking styling notes.
Favorite Daughter
The Irene Dress
ZARA
Combination Mini Dress
Made for tights and boots.
Reformation
Lani Knit Dress
Amanda Uprichard
Isla Dress
ZARA
Midi Dress With Tied Knot
It’s the tie detail for me.
DÔEN
Graciela Tiered Corded Lace-Paneled Ramie Midi Dress
The perfect under-$100 fall dress.
Reformation
Edalene Dress
NA-KD
Fine Knitted Maxi Dress
You can just tell this is cozy.
Reformation
Josefina Knit Dress
Simple and sophisticated.
MANGO
Short Dress With Lapel
FAITHFULL THE BRAND
Artemi Knit Dress
Chocolate brown always looks elevated.
MANGO
Asymmetrical Dress With Gathered Details
This dress looks significantly more expensive than it is.
Reformation
Kendi Denim Midi Dress
I didn’t know I needed a denim maxi dress until now.
Lioness
Field of Dreams Long Sleeve Maxi Dress
I just love the pleating details.
Free People
Butterfly Babe Midi Dress
A very chic mix of polka dots and lace.
ZARA
Textured Short Dress
Reformation
Nemy Knit Dress
The fall version of the LBD.
