| dressed for fall | How You Can Wear All Your Favorite Summer Dresses Well Into Fall


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

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 TurtleneckSonga 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.

Reformation Winslow Dress

AGOLDE Cigarette Jean from Amour VertEverlane 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 HeelReformation 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 TerryNisolo 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 VertYellow 108 Benny Fedora

The Pleated Dress

Give this pretty summer staple a fall facelift with a parka and metallic booties.

Ulla Johnson Sonja Dress

Everlane The City AnorakBrother Vellies Rose Gold Bianca Boot

Bell Sleeves

Restyle this comfy and cute style for fall with a an oversized vest and chelsea boots.

Doen Le Marche Dress

Elizabeth Suzann Clyde VestR.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 CardiganMatt & 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

Swedish Stockings Andrea Smoking TightsBeyond 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 MulesLevi’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 JacketEtiko 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 JacketVeroVerto Recro Accordion from Amour Vert


Give your favorite LWD new life with a cool fall-colored blazer and closed-toed shoes.

Reformation Mariposa Dress

Bless The Mess Charming Blazer from Alma SantaCoclico Aframe Oxfords from Amour Vert


What is your favorite way to transition your favorite summer dress into fall?


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