20 chic and comfortable fall dresses you'll want to wear all season long

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While it’s definitely sad to say goodbye to summer beach days, there’s nothing like fall foliage and chic autumn fashion. Even if you love spending time in the sun, it’s hard not to get excited about Halloween costumes and incorporating all of your fall outfits back into your wardrobe!

Before you get ahead of yourself and unpack all of those heavy wool sweaters, you’ll need a few great summer-to-fall transition pieces to upgrade your look. And this season, it’s all about dresses.

To help you shop some of the best strappy slips, flattering midis and more on the market, we rounded up 20 great options you’re bound to love.

Women’s fall dresses

Gap Factory Quarter-Zip Sweatshirt Dress

Gap Factory Quarter-Zip Sweatshirt Dress

Gap Factory Quarter-Zip Sweatshirt Dress

Gap Factory Quarter-Zip Sweatshirt Dress $35.99 at Gap Factory

Keeping it casual applies to dresses, too. This quarter-zip fleece sweatshirt dress is great for a day of running errands, brunching with friends or just lounging around the house.

Who What Wear Balloon Long Sleeve Dress

Who What Wear Balloon Long Sleeve Dress

Who What Wear Balloon Long Sleeve Dress $39.99 at Target

Just because winter is around the corner doesn’t mean you have to stay clear of fun patterns! This adorable long-sleeve dress from the Who What Wear collection at Target comes in three floral designs that are perfect for the new season.

Lulus Spot Me White Polka Dot Short Sleeve Midi Dress

Lulus Spot Me White Polka Dot Short Sleeve Midi Dress

Lulus Spot Me White Polka Dot Short Sleeve Midi Dress $39.00 at Lulus

This polka dot dress is another great fall option from Lulus. The form-fitting bodice and A-line silhouette is extremely flattering, and the subtle design is perfect for layering with a neutral cardigan when the temperature drops. The best part — it’s currently over 40% off!

A New Day Long Sleeve Ribbed Knit Sweater Dress

A New Day Long Sleeve Ribbed Knit Sweater Dress

A New Day Long Sleeve Ribbed Knit Sweater Dress $29.99 at Target

You can’t go wrong with a classic sweater dress in the fall. Try accessorizing this cute midi-length option with your favorite jewelry, crossbody bag and some booties.

H&M Knit Sweater Vest Dress

H&M Knit Sweater Vest Dress

H&M Knit Sweater Vest Dress $24.99 at H&M

Sweater vests are all the rage this season. Give the trend a try in this unique dress style — wear it alone or layer over tights and tall boots for a more seasonal look.

Old Navy Sleeveless Floral-Print Mini Swing Dress

Old Navy Sleeveless Floral-Print Mini Swing Dress

Sleeveless Floral-Print Mini Swing Dress

Old Navy Sleeveless Floral-Print Mini Swing Dress $39.99 at Old Navy

This cozy swing dress from Old Navy is great because you can wear it on its own in the warmer months and then with a light jacket and tights when it gets colder.

Zara Floral Print Dress

Zara Floral Print Dress

Zara Floral Print Dress $49.90 at Zara

This floral midi dress would pair perfectly with a brown leather bag and some matching mules. We’re obsessed with the bold print and trendy tiered skirt.

J.Crew Classic-Fit Crisp Cotton Poplin Shirtdress

J.Crew Classic-Fit Crisp Cotton Poplin Shirtdress

J.Crew Classic-Fit Crisp Cotton Poplin Shirtdress $118.00 at J.Crew

J.Crew is full of great fall staples. This classic shirtdress with an adjustable sash and button-down detailing can be worn on its own or paired with tights later on in the season. We love the classic neutral shade, but you can score the same dress for almost half the price if you’re more into the Navy Stripe or Pink Blue Plaid options.

Forever 21 Sweater-Knit Wrap Dress

Sweater-Knit Wrap Dress

Sweater-Knit Wrap Dress $29.99 at Forever 21

This chunky sweater dress from Forever 21 is chic, warm, simple and budget friendly. It features stylish batwing sleeves and a subtle open-back design that will have plenty of onlookers asking where you got it.

J.Crew Smocked Puff-Sleeve Dress

J.Crew Smocked Puff-Sleeve Dress

J.Crew Smocked Puff-Sleeve Dress $128.00 at J.Crew

If you love compliments, this dress is sure to get you plenty of them! This smocked puff-sleeve number can easily be paired with heels but would also look great with your favorite white sneakers for a more casual look.

Zesica Bohemian Floral-Printed Wrap Maxi Dress

Zesica Bohemian Floral-Printed Wrap Maxi Dress

Zesica Bohemian Floral-Printed Wrap Maxi Dress $30.59 at Amazon

We totally love this bohemian wrap dress for those who live in the warmer parts of the country. This red pattern would look super chic with sandals or booties.

Unbranded Long-Sleeve Pocket T-Shirt Dress

Unbranded Long-Sleeve Pocket T-Shirt Dress

Unbranded Long-Sleeve Pocket T-Shirt Dress $31.99 at Amazon

This dress has over 10,500 verified five-star ratings on Amazon, with many people saying how much they love this piece as a fall staple in their closet. It’s available in this festive floral pattern and 29 other designs.

R. Vivimos Cotton Tie-Waist Sweater Dress

R. Vivimos Cotton Tie-Waist Sweater Dress

© Amazon R. Vivimos Cotton Tie-Waist Sweater Dress (Amazon / Amazon)

R. Vivimos Cotton Tie-Waist Sweater Dress $28.99 at Amazon

This chic tie-waist sweater dress has over 7,300 verified five-star ratings. It combines comfort and style for a look that’s perfect for everyday wear. Throw on a pair of sneakers or low-heeled booties and you’re set!

Lapel V-Neck Button Shirt Dress

Lapel V-Neck Button Shirt Dress

© Walmart Sleeveless Floral-Print Mini Swing Dress

Lapel V-Neck Button Shirt Dress $33.22 at Walmart

This breezy and budget-friendly maxi dress is as easy as they come. Wrap up your look with a belt and matching boots and prepare to take on the day, whether that means brunch or the farmers market — the possibilities are endless.

Mitilly Women’s V-Neck Ruffle Swing Dress

Mitilly Women’s V-Neck Ruffle Swing Dress

© Amazon Mitilly Women’s V-Neck Ruffle Swing Dress (Amazon / Amazon)

Mitilly Women’s V-Neck Ruffle Swing Dress $30.99 at Amazon

Spruce up your return-to-office wardrobe and consider trying this trendy swing dress. This burnt orange shade would look great on any skin tone, but it’s also available in other versatile colors and patterns like plaid and checkered.

Belongsci Bell Sleeve Shift Dress

Belongsci Bell Sleeve Shift Dress

© Amazon Belongsci Bell Sleeve Shift Dress (Amazon / Amazon)

Belongsci Bell Sleeve Shift Dress $32.99 at Amazon

This bell-sleeve shift design is the little black dress every woman should have in her closet.

Umgee Boho Bliss Dress

Umgee Boho Bliss Dress

© Amazon Umgee Boho Bliss Dress (Amazon / Amazon)

Umgee Boho Bliss Dress $17.99 at Amazon

For those looking for a fun, frilly and bohemian style this fall, consider this mini dress from Umgee. It comes in seven different colors and features flowing mid-length sleeves.

Grecerelle Short Sleeve Slit Maxi Dress

Grecerelle Short Sleeve Slit Maxi Dress

© Amazon Grecerelle Short Sleeve Slit Maxi Dress (Amazon / Amazon)

Grecerelle Short Sleeve Slit Maxi Dress $28.04 at Amazon

For a simple but sleek option, you won’t regret this short-sleeve maxi dress. The matching belt cinches in the waist, and the tasteful slit can help elongate your legs.

Fancyinn Shift Dress With Pockets

Fancyinn Shift Dress With Pockets

© Amazon Fancyinn Shift Dress With Pockets (Amazon / Amazon)

Fancyinn Shift Dress With Pockets $38.99 at Amazon

This shift dress is a great piece to throw on if you want to look put-together but don’t have the time or effort to find an over-the-top outfit.

Romwe A-Line Corduroy Overall Dress

Romwe A-Line Corduroy Overall Dress

© Amazon Romwe A-Line Corduroy Overall Dress (Amazon / Amazon)

Romwe A-Line Corduroy Overall Dress $20.99 at Amazon

Corduroy will never go out of style! This cute overall dress from Romwe comes in 19 different colors, including this fall-friendly burgundy shade.

For more stories like this, check out:

  • Take it from the pros — these 12 pieces are what you need in your fall wardrobe
  • Target’s Fall Designer Collection is live — and is already selling out fast
  • Clogs are the unofficial shoe of fall — 14 pairs to wear this season
  • 19 cute and trendy plus-size dresses you need for fall
  • How to rock a matching set, according to stylists — plus 14 options to try

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This article was originally published on Sept. 15, 2020.

dresses for the fall season
dresses for the fall season
j crew shirt dress
j crew shirt dress
green short sleeve maxi dress
green short sleeve maxi dress
dresses by vivimos
dresses by vivimos
3/4 sleeve shift dress
3/4 sleeve shift dress
gap factory women dresses
gap factory women dresses
balloon sleeve dresses for women
balloon sleeve dresses for women
day dresses for senior women
day dresses for senior women

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