Fall-Friendly Maxi, Midi, and Mini Dresses Start at Just $19 During Amazon’s Massive Labor Day Sale

That sudden chill setting in each evening can only mean one thing: Layering season is upon us. If you're looking to refresh your wardrobe with versatile pieces that seamlessly transition from summer to fall, Amazon has you covered with stylish dresses on sale this Labor Day weekend.

We rounded up 15 summer-to-fall dresses to fashionably usher you into the next season. Enjoy discounts of up to 51 percent off on maxis, midis, and minis that you can wear on their own now and with a jacket on top once the temperature drops. The best part? These Amazon dresses are all on sale for less than $50. 

Amazon’s Best Summer-to-Fall Dress Deals

• Zesica Flutter-Sleeve Tiered Midi Dress, $32.89 (orig. $66.99)
• Grace Karin Tie-Waist Midi Dress, $39.09 with coupon (orig. $45.99)
• Btfbm Bodycon Mini Dress, $25.69 (orig. $31.99)
• Prettygarden Wrap Maxi Dress, $47.99 (orig. $60.99)
• Zesica Tie-Strap Maxi Dress, $45.89 with coupon (orig. $66.99)
• Grace Karin Halter-Neck Maxi Dress, $34.59 (orig. $51.99)
• Wneedu Button-Down Midi Dress, $30.50 (orig. $33.89)
• Hdlte Bodycon Knit Midi Dress, $28.79 with coupon (orig. $36.99)
• Zesica Smocked Prairie Dress, $32.98 (orig. $57.99)
• Qinsen Tennis Mini Dress, $32.35 (orig. $45.99)
  

Zesica Flutter-Sleeve Tiered Midi Dress

This tiered midi dress has a flattering fit with a smocked bodice and short, flutter sleeves. Wear it during the last few weeks of summer with strappy sandals, and keep it in your outfit rotation this fall with a cardigan or denim jacket layered on top. 

Grace Karin Tie-Waist Midi Dress

From its cap sleeves to elegant midi-length hem, this tie-waist dress is the epitome of chic. A perfect choice for any occasion where you need to look polished and put together. 

Btfbm Bodycon Mini Dress

This best-selling bodycon mini dress with a cross-over hem is easy to throw on and style –– a closet staple guaranteed to make you feel great every time you wear it. It comes in 36 colors and has more than 25,000 five-star ratings (yes, really). 

Prettygarden Wrap Maxi Dress

You can’t go wrong with a classic wrap dress. This flattering maxi version comes in 36 patterns, from boho florals to graphic prints, and has more than 8,000 five-star ratings. 

Zesica Tie-Strap Maxi Dress

A smocked bodice and tied straps ensure this maxi dress will fit you like a glove. It comes in 24 colors, including both neutrals and bright shades, and has been purchased more than 100 times in the past month. 

Grace Karin Halter-Neck Maxi Dress

If you have a wedding or beach vacation on the horizon, this halter-neck maxi is a smart purchase. You can always throw on a blazer or denim jacket when the temperature dips. 

Wneedu Button-Down Midi Dress

This button-down sundress with fluttery sleeves and a knee-length hem is an instant throw-on-and-go staple. It comes in a huge array of prints, including lemons and abstract florals, and it even has hidden pockets to carry your essentials. 

Hdlte Bodycon Knit Midi Dress

When fall officially hits, this bodycon midi dress made from a stretchy knit fabric will be your new favorite outfit. Team it with a leather jacket and ankle boots for a casual weekend look. 

Zesica Smocked Prairie Dress

Give the prairie dress trend a whirl with this gingham midi version. Thanks to its puff sleeves and smocked bodice, the dress has a traditional vibe, but a leather jacket and simple block heels will add balance and contrast to your look. 

Qinsen Tennis Mini Dress

Yes, technically this is a tennis dress, but we think the silhouette would look equally cool off the court. It has a built-in bra for comfortable support and shorts underneath, so you don’t have to worry about anything showing through. 

Dokotoo Ruffle-Hem Maxi Dress

If you’re a fan of bold prints, then this ruffle-hem maxi dress belongs in your closet. The frock comes in 10 variations, including daisies, geometric patterns, and diamond motifs in vibrant, eye-catching colors.  

​​Marzxin T-Shirt Midi Dress

If you’d describe your style as effortless, add one of these T-shirt dresses to your cart. Whether you’re lounging around at home or meeting friends for a casual meal, it’s a comfortable yet stylish choice.

Merokeety One-Shoulder Midi Dress

This one-shoulder midi dress comes in 14 colors, including fall-appropriate caramel and coffee hues. Dress it up with heels and delicate jewelry or down with ballet pumps and a jacket.

Aedceal Trapeze Mini Dress

The loose and flowy fit of this trapeze mini dress makes it a comfortable option to reach for when you’re running errands or relaxing at home. While it's a great breezy option for summer, it easily transitions to fall with a denim jacket, tights, and boots. 

The Drop Ana Silky V-Neck Midi Slip Dress

Meet your new favorite going-out dress. Spaghetti straps and a V-neckline give this slip dress a ‘90s-inspired feel that would pair perfectly with a shoulder bag and kitten heels.