Believe it or not, fall is just around the corner (where did the time go?!). Although we’ll soon be switching to sweater weather, I have no intention of abandoning my warm-weather wardrobe. After all, heat waves often linger past Labor Day, so I’m holding onto a few lightweight essentials that can transition between seasons—namely, my rotation of summer dresses.
For hot autumn days spent in the office, I’ll wear a sleeveless shirt dress paired with mesh ballet flats. And when temperatures cool in the evening, I’ll cover my shoulders with a sleek blazer suitable for after-work happy hours. Meanwhile, for casual outings like pumpkin patch trips and farmers' market visits, a smocked dress works well with knee-high boots and a denim jacket.
Bottom line? There are countless ways to style a summer dress for fall. So, go ahead and keep scrolling to see every dress I’ll be wearing—and layering—this upcoming season. From beloved favorites that I already own to must-have pieces high on my wish list, I promise these items will hold your transitional outfits together.
Dive into the polka dot trend with Mango’s collared shirt dress. Wear this style to work and look forward to charming compliments from your coworkers.
If you’re interested in which color trends are expected to become popular this fall, let me guide you to chocolate brown. Featured on the Fall 2025 runways of Ferragamo, Gucci, and Hermès, this charming shade will soon be in your wardrobe.
For a sophisticated vibe, slip into Aritzia’s midi dress made from luxurious satin. Be sure to finish your look with kitten heels.
Gingham dresses have become a staple in my wardrobe this season. When temperatures drop, I plan to wear Veronica Beard’s Mackey dress with a classic trench coat and slingbacks.
Yes, you can wear white dresses after Labor Day. Just style this look with cold-weather trends like suede jackets and riding boots.
Florals for fall? It’s actually not that groundbreaking. Dôen makes the classic print feel more autumn-forward with earthy tones.
What I love most about Madewell’s crochet dress is its contrasting design that adds a touch of drama. Consider this piece if you’re not afraid to stand out from the crowd.
Channel your inner Jackie O with this mod dress from Reformation that exudes "retro' style.
As a fan of ‘90s fashion, I love a satin slip dress more than anything. Katie May's version showcases a sleek champagne hue that's so refined.
If you know me well, you’ve probably seen me in Rails’s Genevieve dress. What can I say? It's incredibly versatile! I can’t wait to keep wearing this look for many more brunches and date nights.
When temperatures rise above 80 degrees, you’ll want to wear J.Crew’s tiered maxi dress. It’s made from cotton, so you’ll stay comfortable and cool.
Right now, Everlane is holding a big sale. This dress just dropped from $158 to $87. So, if you like it, act quickly!
A.L.C’s Angelina dress will turn heads with its plunging V-neckline and flowing smocked bodice.
Whimsical bubble hemlines aren’t going anywhere. Try the trend with All the Ways’s Aria dress, which looks sophisticated layered under a cozy cardigan.
If you want to avoid spending a lot on your next dress, try Free Assembly’s eyelet midi. Priced under $40, this style is affordable.
