A woman in the FREE PEOPLE Perfect Storm Midi Dress leans against a wall while smiling and relaxing. Embracing the Summer to Fall Dresses trend, she holds a brown bag and stands in a narrow street with colorful buildings in the background.

FREE PEOPLE

The Dress Edit

I’ve Just Found The Prettiest Designer Summer To Fall Dresses

Ready to shop all the best summer to fall dresses from your favorite designers? Me too. Somehow, fall is less than a month away, but I’m not ready to give up on midi, maxi, or even mini silhouettes. Luckily, for those as dress-obsessed as I am, I’ve found so many pretty and versatile options. Every dress on this hand-picked list will see you stylishly through the rest of summer and into the season ahead. Oh, and get ready to swap your beach shoes for boots and straw bags for leather ones too. I’ve selected all the prettiest shoes and bags to go with every dress.

A person with curly hair wearing the flowy EMPORIO SIRENUSE Lavinia Printed Silk-chiffon Midi Wrap Dress 2 sits barefoot on the edge of a wooden boat. The background features a rocky shoreline with trees and blue water on a sunny day.

Emporio Sirenuse

A person stands in front of a dark brick wall, wearing one of this year's stylish summer to fall dresses— the FREE PEOPLE Ultraviolet Dress, featuring a white fabric adorned with black polka dots. They complement the look with black shoes and patterned socks. With long hair cascading down, they gaze toward the camera while the sun casts shadows on the ground.

Free People

You Can Never Go Wrong With Maxi Summer To Fall Dresses

If there’s one thing I always look out for when shopping summer to fall dresses, it’s length. Ankle-length dresses are so versatile and transition seamlessly between the seasons. How? With a simple shoe switch-up. For example, the Ultraviolet maxi dress by Free People. Firstly, this adorable criss-cross-back maxi dress has a classic black and white polka dot print. So, it’ll stay in style not just season to season but year to year too. Secondly, it’ll look amazing with a cute pair of sandals or even low heels for the end of summer. Then, when fall arrives, it’ll look just as good with a pair of ballet flats or boots and a cute bag to match. My recommendation? Style yours with the buckled leather ballerina shoes by Mui Mui and Rose Marie lazer-cut leather bucket bag by Alaia.

The Lavinia printed silk-chiffon midi wrap dress by Emporio Sirenuse is also high on my must-have list. I adore the subtle yet playful horse print and the flattering shirred waist. Not to mention the chic wrap top and ankle-length skirt that’ll look amazing with flats and boots this fall. Until then, I’ll be styling this dress with sleek, neutral sandals and a coordinating bag. Most likely the Allington straw tote by Allsaints and the Almost Bare crystal-embellished PVC sandals by Aquazzura.

 

 

Shop more summer to fall dresses selected and reviewed by our expert fashion buyers and stylists

  • FAITHFULL THE BRAND Jardin Midi Dress

    $210
  • FREE PEOPLE Perfect Storm Midi Dress

    $168
  • FREE PEOPLE Ultraviolet Dress

    $148
  • AJE Cohort Mini Dress

    $455
  • AJE Catalyst Pleated Midi Dress

    $595
  • AJE Arris Fringed Maxi Dress

    $595
  • GOLDEN GOOSE Journey Denim Midi Dress

    $610
  • DÔEN Arleen Dress

    $298
  • EMPORIO SIRENUSE Bella Batik Tiered Ruffled Printed Embroidered Cotton-voile Maxi Dress

    $1,175
  • EMPORIO SIRENUSE Lavinia Printed Silk-chiffon Midi Wrap Dress

    $2,200
  • CAMILLA Embellished Lace-trimmed Printed Silk Crepe De Chine Maxi Dress

    $999
  • ETRO Floral-print Off-shoulder Cotton Dress

    $6,088
  • MAC DUGGAL Sleeveless A-Line Midi Dress

    $458
  • MAC DUGGAL Long-Sleeve Ruffled Mini Dress

    $398
  • ANTHROPOLOGIE The Katerina Button-Front Dress

    $178
  • FREE PEOPLE Sundrenched Floral Tiered Maxi Sundress

    $168
  • ZIMMERMANN Net Sustain Lexi Floral-print Linen Midi Wrap Dress

    $795
  • ETRO Belted Floral-print Silk-crepon Maxi Dress

    $4,650

Strappy Summer To Fall Dresses Perfect For Layering

As the weather starts to cool off and evenings start to require an extra layer, make strappy summer-to-fall dresses your go-to. Perfect for daytime sun and easy to throw knitwear over at night, these dresses are as pretty as they are versatile. You won’t find a more classic slip-on silhouette than the Jardin midi dress by Faithfull The Brand. With a sleek V-neckline, wide shoulder straps, and a timeless blue and white print you’ll want to wear this dress on repeat until winter. Especially with the Ella crochet tote by Tory Burch and Mary Jane Shelly flats by Jeffrey Campbell.

If you’re looking for an A-line silhouette instead, choose the sleeveless floral midi dress by Mac Duggal. I’m head over heels for this ditsy printed dress with ruffle tiers and a chic strappy neckline. Style this with the Cala Di Volpe sandals by Aquazzura and Givenchy’s small VoYou belted leather tote for summer. Then, add boots and light, block-color layers when fall arrives.

Shop All Summer To Fall Dresses

Person in a sleeveless, white FAITHFULL-THE-BRAND-Jardin-Midi-Dress with a blue floral pattern stands against a plain wall. Their hair is pulled back, and they are wearing black sandals. One arm is raised to shield their eyes from the sun, showcasing one of the stunning Summer To Fall Dresses of the season.

Faithfull The Brand

A woman wearing the MAC DUGGAL Sleeveless A-Line Midi Dress is posing against a plain background. This dress, ideal for the Summer to Fall transition, features a v-neckline and a hemline that falls below the knees. She pairs it with strappy high-heeled sandals and has long, dark hair cascading down. One hand is gracefully holding a part of the dress.

Anthropologie

I’m A Fashion Editor Who Loves Fall: Here’s My Top 5 Ways To Style A Black Dress Next Season