One of my absolute favorite things about summer is how easy it can be to get dressed. Throw on a cute printed midi or a flowy maxi dress and some sandals and you’re good to go.
One of my other favorite things about summer is how freakin’ cute all of the those summer dresses are — I mean, c’mon, fun florals, flirty ruffles, bright colors and breezy silhouettes, does it get any better?
So it’s no surprise that it’s rather upsetting when that first chilly day rolls into town and surprises you with colder temps. But don’t fret, I’ve rounded up 14 ideas for wearing your favorite summer dresses well into the fall season.
#winning
1) It’s like doubling your wardrobe AND 2) You’ll get maximum wear out of all your summer favorites, because our clothes should be able to live for multiple seasons.
The Floral Midi
What was once your go to with strappy sandals during the summer is easily updated with chunky booties and a knee length coat for a fresh fall update.
Everlane The Suede Heel Boot, Everlane The Belted Wool Shawl Coat
The Cotton Cross Back Dress
Perfect for summer because it’s so light and airy, update the look for fall by styling with a t-shirt of turtleneck underneath. P.S. You can keep the basket bag.
Everlane Clean Cotton Cross Back Dress
Amour Vert Flannery Turtleneck, Songa Designs International Infinity Handbag from Good Cloth
The Wrap Dress
Style that wrap dress you wore everywhere this summer over denim for a cool new look for fall.
AGOLDE Cigarette Jean from Amour Vert, Everlane The E2 Shine Modern Oxford
The Patterned Midi
The colors were perfect for summer, but the length is great for fall’s chillier weather. Add smart pumps and button front blazer to make this puppy totally fall-ready.
Mara Hoffman Cut Out Midi Dress
Rachel Comey Fonda Heel, Reformation Besos Jacket
The Slip Dress
Take your slip dress into the next season by wearing with a cozy sweatshirt and sneakers.
Organic by John Patrick Bias Long Slip Dress from The Dreslyn
Everlane The Slim Classic French Terry, Nisolo Elayna Sneaker
The Flowy Maxi
Nothing screams summer like a breezy maxi, but add a good moto jacket, a wool fedora and some ankle boots to make your outfit scream fall instead.
People Tree V&A Tulip Print Gathered Dress
Deadwood Classic Biker Jacket from Amour Vert, Yellow 108 Benny Fedora
The Pleated Dress
Give this pretty summer staple a fall facelift with a parka and metallic booties.
Everlane The City Anorak, Brother Vellies Rose Gold Bianca Boot
Bell Sleeves
Restyle this comfy and cute style for fall with a an oversized vest and chelsea boots.
Elizabeth Suzann Clyde Vest, R.M. Williams MIllicent Boot
The Shirt Dress
Swap your sandals for some low-top sneakers and a cardi for an easy overhaul of this summer staple.
Everlane The Cotton Pocket Shirt Dress
Everlane The Oversized Ribbed Wool-Cashmere Cardigan, Matt & Natt Berri Sneaker
The Flared Mini
Take this epitome-of-summer frock into the colder temps by adding tights and over-the-knee boots.
Swedish Stockings Andrea Smoking Tights, Beyond Skin Ronnie Black Stretch Boots
The Ruffled Midi
Introduce your this breezy chiffon beauty to a new season with chunky mules and an oversized denim jacket.
Rue Stiic Andalusia Dress from Alma Santa
Rachel Comey Scarpa Polished Black Mules, Levi’s The Sherpa Trucker Jacket (yea, I stole this one from the boys, so sue me)
The Knit Dress
Add high tops and a bomber to this classic silhouette to make it feel new again this fall.
Everlane The Micro Rib Cami Dress
Christy Dawn The Chandler Jacket, Etiko Organic Fairtrade Sneakers Hitop White
The Lace Midi
Pair with black accessories and leather jacket to carry this looker into the autumn season and an edgier scene.
Aijek Padua Off Shoulder Dress
Better World Fashion Dayna Vintage Biker Jacket, VeroVerto Recro Accordion from Amour Vert
The LWD
Give your favorite LWD new life with a cool fall-colored blazer and closed-toed shoes.
Bless The Mess Charming Blazer from Alma Santa, Coclico Aframe Oxfords from Amour Vert
What is your favorite way to transition your favorite summer dress into fall?
b.good 