22 Chic Summer To Fall Dresses To Wear Now + Later
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Summer is coming to a close, but that doesn’t mean your summer dresses have to. It might not be bikini season any more, but dresses will still be in full effect. Fall is that special season where the weather meets you right in the middle—not too hot and not too cold. (Of course, this is dependent on where you reside!)
However, give your summer dresses a second chance because they can still be a part of your fall wardrobe. Wearing dresses during the fall is just as stylish and comfortable as during the summer season. So, feel free to transition into this new season with these chic summer to fall dresses that are perfect for both seasons.
Our Dress Picks Transitioning From Summer To Fall
Image: Reformation
Polka Dot Maxi Dress
Reformation
Price Range: $$$
Feel like Julia Roberts in “Pretty Woman” in this classic brown polka dot midi-dress that is perfect for summer and fall. It can be dressed “up” and “down” for a more casual look or a fancy night out. Reformation is also a sustainable brand, so be eco-friendly and stylish in this classic dress!
Image: Amazon
Red Floral Mini Dress
Relipop
Price Range: $
This red floral mini dress from Relipop is comfortable for a summer vacation and perfect for a fall day at a winery. The floral print is timeless along with the side bow and ruffles at the end. Depending on how you style it, this dress works all year long. The price is also hard to say no to!
Image: Nordstrom
Emma Sundress
Nom Maternity
Price Range: $$ - $$$
This versatile maternity sundress is light and airy for the warm, summer outings and breezy, fall afternoons. For the soon-to-be mothers, this comfortable sundress with its light blue color is easy to pair with a light cardigan or chic, leather jacket for both seasons. This dress will easily become a staple in your closet.
Image: Madewell
Organic Cotton Crewneck Striped Midi Dress
Madewell
Price Range: $$
This simple striped cotton dress was perfect to wear to the beach, but it will also be perfect under some Fall foliage. The rusty color matches the mood of the Autumn months. Although sleeveless, pair it with your favorite chunky sweaters or cardigans along with your favorite ankle boots for a comfortable and cute fall outfit.
Image: ASTR The Label
Floral Asymmetrical Midi Dress
ASTR The Label
Price Range: $$
Ruffles and puffy sleeves will be a top fashion trend all year long. The puffy sleeves and airiness of this dress made it comfy for summer, but layer it up this fall with scarves and maybe even a beret during these upcoming cooler months.
Image: Urban Outfitters
Layla Lace Corset Mini Dress
Urban Outfitters
Price Range: $$
This sexy little dress does not have to be tucked away this Fall. The bright color and length of the dress might be more summer appropriate, but wear it with a leather jacket, boots, and trendy cowboy boots and you are ready for a girls' night out with this fall dress!
Image: Girlfriend Collective
Naomi Workout Dress
Girlfriend Collective
Price Range: $$
This versatile workout dress from Girlfriend Collective was probably worn many times for summer workouts and brunches, but know that you can wear it as many times this fall. Maybe going on a fall bike ride or going to the farmer’s market for a chill Saturday, this is an easy statement piece to style making this dress worth the price.
Image: Old Navy
Halter Maxi Dress
Old Navy
Price Range: $
Don’t let the halter design stop you from wearing a dress like this during the cooler autumn months. This low-price, midi-black dress is the perfect length appropriate for all seasons. Pull out your sherpa-lined denim jacket and black ankle booties for your new favorite fall outfit.
Image: Nordstrom
Checkered Long Sleeve Cotton Dress
Topshop
Price Range: $$
Although this dress came out during the summertime, the checkered and plaid-like dress seems more appropriate for fall. Wear this dress for a fall date night with your favorite leather boots and if the weather permits, no jacket is needed, so show off this fall dress as-is!
Image: Amazon
Boho Black Floral Dress
Milumia
Price Range: $
This affordable black floral dress with its flowing design is a perfect summer to fall dress. The floral print has more of a tropical feel, which fits perfectly for summer, but a black backdrop keeps it functional for fall. The black and bright-colored flowers also mean that a variety of shoe colors can match. The midi dress also comes with an affordable price. What other reason do you need to include it in your closet?
Image: Amazon
Brown Ruched Bodycon Dress
BTFM
Price Range: $
This mild, chocolate brown color has become more popular during this summer season and its warm feel is fitting for the fall season. The simple bodycon can be accessorized in so many ways and the styles are endless—this is why the dress is on the list. For example, the mini-dress can be an easy cover-up as you take a trip to the beach or pair it with a wide-brimmed hat, cardigan, and booties. Also, Amazon offers a variety of colors to choose from, but brown is a guaranteed stylish dress that you can make your own during the summer and fall seasons.
Image: ASOS
Satin Wrap Dress
ASOS
Price Range: $
Any fancy fall events? The golden-like yellow is an ideal summer color but offers a warm tone perfect for fall. This satin wrap dress can be dressed up and down! Wear it to a fall wedding with golden heels or a coffee date with your best friend paired with sneakers.
Image: Aeropostale
Notch Neck Tie Dress
Aeropostale
Price Range: $
This notch-neck style became a big trend during the warmer months of spring and summer but will continue into fall. The light blue floral print can be paired nicely with deeper, warmer, and darker colors into the new season.
Image: Zaful
Gingham Puff Sleeve Dress
Zaful
Price Range: $
Prints are here to stay, remember? This beige-gingham print dress is a fun summer-to-fall dress to add to your wardrobe. The puff sleeves give it an extra chic look along with the ruffles at the end of the dress. The dress will hug you in all the right places and accentuate any curves. The color, print, and bodycon style make it easy to wear during “hot girl summer” and taking it into fall.
Image: ASTR The Label
Mona Tie Strap Mini Dress
ASTR The Label
Price Range: $$$
You can’t forget a satin slip dress can be worn all summer and into fall. You most likely will just need a sweater or jacket to pair it with for the colder season. This mini satin dress can be paired with sneakers for a stylish casual look for both summer and fall, especially in this green color. Dress it up in the evening with heels or a pair of black booties. The style ideas with this dress are endless which is why it’s on the list and making it a perfect summer-to-fall dress!
Image: Amazon
Fields of Gold Dress
BB DAKOTA
Price Range: $
Yes, you can wear white after Labor Day. This summer-to-fall dress is a great reminder to do so! The loose-fit and t-shirt style makes it easy to create stylish outfits. This dress is like a blank canvas, so have fun with fall-colored accessories.
Image: SSENSE
Beige Trail Midi Dress
Holzweiler
Price Range: $$
The see-through and transparent look became more popular in fashion this year too. Wear this trendy woven dress to a music festival or when you want to show out. The stretchy material makes it perfect to dance all night in!
Image: Nordstrom
Midi Sundress
House of CB
Price Range: $$
Feel extra pretty in pink with this summer-to-fall sundress! Although a sundress, it is versatile enough for fall such as an autumn wedding or any special event before the year ends!
Image: Nordstrom
Colorblock Sundress
AllSaints
Price Range: $$
Taking a trip abroad? This is the dress you’ll want to wear to be a fashionista this fall. Color-blocking is another fun clothing trend that got popular throughout the year, so don’t let these bright colors hide away this fall.
Image: Nordstrom
Tiered Cut-Out Maxi Dress
LOST + WANDER
Price Range: $$
Tiered dresses were worn all summer long and can be worn all fall if styled well! Think coats, boots, scarves, and hats. Also, the tan and brown-like colors are great for fall.
Image: Revolve
One Shoulder Jersey Dress
Seafolly
Price Range: $$
One-strap tops and asymmetrical designs are staying all of 2022, so don’t hide them away just because the temperature is going down. This simple one-shoulder cotton dress will be a closet staple even into 2023.
Image: Red Dress Boutique
Dark Emerald Tunic
Red Dress Boutique
Price Range: $$
This dress is classic and great for any season. Maybe during summer underneath is a colorful bikini but for fall layer it with a timeless, tan trench coat and your favorite heels. This dress makes it easy to go from summer casual to fall chic quickly!
