17 Comfy, Summer-to-Fall Dresses Under $40 on Amazon

Seasons come and go, but one thing’s for sure: Dresses are a year-round wardrobe staple. To prep for transitional weather, we’re restocking our wardrobes with breezy, ultra-flattering dresses that can be styled with sandals, sneakers and even boots.

Our favorites are comfy, classy and ultra-versatile, ideal for everything from coffee runs to in-office meetings. Even better, they don’t break the $37 mark, making them the ultimate balance of stylish and affordable. These staples are selling out as we speak!

17 Comfy, Late-Summer Dresses to Wear Through September

Brunch-to-Errand Dresses

1. Our Favorite: Everything about this long-sleeve dress is chic, from the textured material to the swoon-worthy blue hue. You’ll look Parisian — guaranteed.

2. Skater Girl: It’s Amazon’s Choice for a reason. This stretchy cotton-blend dress has a weightless feel and secretly wicks sweat.

3. Florals Galore: Billowy and sleek, this short-sleeve number is perfect for vacation, even if you’re just headed to the lake for the weekend.

4. Up or Down: This classy chiffon dress goes from casual to fancy with a quick change of shoes, so we wouldn’t be surprised if you wore it daily.

5. Quiet Luxury: Long-sleeve dresses can feel heavy, but not when they’re made of a skin-friendly modal blend that keeps you as cool as you are sassy.

6. Linen Blend: Channel your inner Hamptons with this tie-strap maxi that features ruffles, pleats and smocking where it matters.

7. The Best $20: This short-sleeve mini should be much more expensive than it is, but we’re not complaining. It begs to be worn with sneakers.

8. Fairytale Vibes: Just trust Us, you’ll look mega-rich in this vibrant paisley-print maxi that’s delicate yet bold.

9. Not Your Typical Crewneck: Give effortlessly put-together energy in this knee-length dress with lantern sleeves and a playful red hue.

Work-to-Wedding Dresses

10. Our Favorite: Confidence-boosting is an understatement with this office-friendly find that cinches without squeezing.

11. European Alert: Be prepared for people to speak French when you wear this belted maxi dress with tiers to lengthen the legs.

12. Guest of Honor: Finally, a dress as colorful as you are. This smocked dress has trendy elbow-length sleeves and a square neckline to show off the collarbone.

13. Swiss Dots: Drapey and sleek, this boho mini is perfect for summer, fall and winter. Just add tights and you’re good to go!

14. Must-Have Maxi: This new drop is destined to sell out. Long sleeves, elevated seams and a flattering high waist are just a few highlights.

15. Zimmermann Who?: With six vintage prints to choose from, we’re tempted to grab a few of these designer-looking lantern-sleeve dresses.

16. Bubble Style: In case you missed it, bubble everything is trendy right now. Nail the look with this slimming tank dress that makes any figure appear hourglass.

17. Accessories, Please: This solid-color midi is a blank canvas for all your favorite jewelry pieces and bags, so have fun with it!