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.
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.
Reformation Temple Dress, $218, Photo Cred Reformation
Reformation Temple Dress
Everlane The Suede Heel Boot, $225, Photo Cred Everlane
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 The Clean Cotton Cross-Back Dress, $98, Photo Cred Everlane
Everlane Clean Cotton Cross Back Dress
Songa Designs International Infinity Handbag, $129 from Good Cloth, Photo Cred Good Cloth
Amour Vert Flannery Turtleneck, $78, Photo Cred Amour Vert
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.
Refoprmation Winslow Dress, $268, Photo Cred Reformtion
Reformation Winslow Dress
AGOLDE Cigarette Jean, $168 from Amour Vert, Photo Cred Amour Vert
Everlane The E2 Shine Modern Oxford, $185 from Everlane
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, $350 from Revolve, Photo Cred Revolve
Mara Hoffman Cut Out Midi Dress
Rachel Comey Fonda Heel, on sale for $145 from Revolve, Photo Cred Revolve
Reformation Besos Jacket, $198, Photo Cred Reformation
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, $189 from The Dreslyn, Photo Cred The Dreslyn
Organic by John Patrick Bias Long Slip Dress from The Dreslyn
Everlane The Slim Classic French Terry Crew, $40, Photo Cred Everlane
Nisolo Elayna Sneaker, $148, Photo Cred Nisolo
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, $195, Photo Cred People Tree
People Tree V&A Tulip Print Gathered Dress
Yellow 108 Benny Fredora, $120, Photo Cred Yellow 108
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.
Ulla Johnson Sonja Dress, $575 from Revolve, Photo Cred Revolve
Ulla Johnson Sonja Dress
Brother Vellies Rose Gold Bianca Boot, $525, Photo Cred Brother Vellies
Everlane The City Anorak, Brother Vellies Rose Gold Bianca Boot
Restyle this comfy and cute style for fall with a an oversized vest and chelsea boots.
Doen Le Marche Dress, $385, Photo Cred Doen
Doen Le Marche Dress
Elizabeth Suzann Clyde Vest, $220, Photo Cred Elizabeth Suzann
R.M. Williams Millicent Boot, $495, Photo Cred R.M. Williams
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.
Everylane The Cotton Pocket Shirt Dress, $78, Photo Cred Everlane
Everlane The Cotton Pocket Shirt Dress
Everlane The Ribbed Wool-Cashmere Oversized Cardigan, $140, Photo Cred Everlane
Matt & Nat Berri, on sale for $54, Photo Cred Matt & Nat
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.
Amour Vert Flavie Dress, on sale for $108, Photo Cred Amour Vert
Amour Vert Flavie Dress
Swedish Stockings Andrea Smoking Tights, $33, Photo Cred Swedish Stockings
Beyond Skin Ronnie Black Stretch Boots, Pre-Order, £165, Photo Cred Beyond Skin
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, on sale for 106€ from Alma Santa, Photo Cred Alma Santa
Rue Stiic Andalusia Dress from Alma Santa
Levi’s The Sherpa Trucker Jacket, $128, Photo Cred Levi’s
Rachel Comey Scarpa Polished Black Mules, on sale for $247.95 from Accompany, Photo Cred Accompany
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, $38, Photo Cred Everlane
Everlane The Micro Rib Cami Dress
Christy Dawn The Chandler Jacket, on sale for $170, Photo Cred Christy Dawn
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, $ from Revolve, Photo Cred Revolve
Aijek Padua Off Shoulder Dress
Better World Fashion Dayna Vintage Biker Jacket, $416, Photo Cred Better World Fashion
VereVerto Recro Accordian in Black, $354 from Amour Vert, Photo Cred Amour Vert
Better World Fashion Dayna Vintage Biker Jacket, VeroVerto Recro Accordion from Amour Vert
Give your favorite LWD new life with a cool fall-colored blazer and closed-toed shoes.
Reformation Mariposa Dress, $198, Photo Cred Reformation
Reformation Mariposa Dress
Bless The Mess Charming Blazer, on sale for 182€ from Alma Santa, Photo Cred Alma Santa
Coclico Aframe Oxfords, $395 from Amour Vert, Photo Cred Amour Vert
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?