As we cruise through August and, dare I say it, approach the end of summer, I'm starting to think about the change of season ahead. Fall is just around the corner, and my shopping cart is already starting to reflect its arrival—most notably in my choice of dresses. While I look to invest in effortless dresses I can wear now in the balmy summer heat, I'm also thinking about dresses that will easily transition into fall.
When shopping for summer-to-fall dresses, consider versatile color palettes and bold prints that can be worn in both seasons. Look for dress silhouettes that shift easily into cooler weather with the right layers and a great pair of boots.
Below, I'm sharing stylish and noteworthy summer dresses that are also perfect for fall, making the transition easy and seamless.
Strapless, waist-cinching silhouettes will continue their dominance into fall.
It's all about boho-chic Chloé vibes this fall. This one is perfect to ease into the season.
A slip dress in a rich dark brown is the perfect transeasonal piece.
This color! This silhouette! Gorgeous.
You can always count on Dôen for the prettiest prints.
This could pass for designer.
Sheer perfection from Mango.
J.Crew's best-selling Gwyneth slip is perfect to wear year-round with the right layers.
A knit dress that will incite all the compliments.
I can't resist these statement puff sleeves.
Paloma Wool always gets it right.
Time to invest in the biggest trend of the season—leopard print.
Perfect for that summer-to-fall transition.
Nineties chic.
So sophisticated.
It's hard to believe this isn't designer.
I'm 100% here for all the boho dresses.
The one I'll be wearing for fall weddings, Thanksgiving, and everything in between.
So good for the price.
An autumnal print to get you in the fall mood.
The color of the season.
A shirtdress that's perfect for summer and fall.
Matteau's dresses are simply stunning.
Charming French-girl vibes.
Another gorgeous Dôen print you can wear year-round.
The LBD you'll reach for when you don't have time to think.
-
I'm a Shopping Director—Simply Put, Here's a Fall Shopping List Filled With Chic, Cool, and Fun ItemsGorgeous sweaters, sleek jackets, beauty staples, and more.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025Exotic finishes! Sock boots! Western motifs!
-
Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do TooSee how fashion people from NYC to Paris to London wear them for fall.
-
My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic Rich-Looking Pieces for Fall 2025Everything is under $100.
-
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.
-
Wait, J.Crew Is 30% Off Sitewide Right Now—These Are the Chic Fall Pieces in My CartThe fall 2025 collection is so good.
-
EverythingBest Knockoff Luxury Clothing Editors Saw, Wore, Did, and Ate During NYFWLet's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.
