The Summer-to-Fall Dresses You'll Keep Wearing Into September

This is the ultimate mini dress that we want to wear all fall. Between the long sleeves and curve-skimming silhouette, the ruffled skirt is just the cherry on top. 

For fall, this is exactly the kind of throw-on piece that makes the summer-to-fall transition so easy to dress for. With a mock neck, draped sleeves, and body-skimming skirt, try styling with tall boots for a playful look that means business. 

Anthropologie's Nuuly Resale marketplace offers gently worn pieces from the rental program, like this mini dress. Available in plus sizes, the $160 dress is now under $20. Note that it's final sale, but we'd wear this versatile staple for years to come. 

Made of a light and breezy cotton-blend, this maxi shirtdress features a collared neckline, button-front closure, and shirred cuffs to help with warmth. Wear it with sandals now, then add knee-high boots and a suede jacket when temperatures drop for a boho-chic look. 

Denim dresses are quintessential for fall, and we anticipate seeing a ton at Fashion Week. Luckily, this marked-down style offers an extra 50% off in your cart. It's made of a cotton blend with an adjustable halter neckline and flared hem for a relaxed boho feel that'll pair well with fall layers, like a knit cardigan. 

The iconic split-toned sweater dress that proves to be popular every sweater season is back again, in a romantic red and pink colorway, all for less than $20. Note that it is final sale, so if you've dreamt of making the colorblock trend yours, now is your best shot. 

Now on sale, the bias-cut midi is made of crinkled Japanese satin with a vintage finish, which is a little more durable that typical satins. Whichever color you choose, it's a wardrobe staple that you can wear anywhere from an outdoor fall wedding to a dressier date night. 

Florals for fall? Not groundbreaking, but classic for good reason. This floral mini dress is an easy way to bring summer silhouettes into fall thanks to its long bell sleeves. The A-line silhouette is cut for a relaxed fit, as comfy as a shift dress, but with a little more shape. Wear it now with ballet flats, and then add leather knee-high boots when fall arrives

Sweater dresses are a sartorial necessity for autumn, and it's no surprise that Madewell has crafted the ultimate pick. This knit midi dress is slightly fitted but relaxed for a comfortable fit that still looks put-together. Save even more with the code LONGWEEKEND for an extra 30% off–valid this weekend only. 

Between the elongated sleeves and neutral plaid pattern, this on-sale piece might take the title as the "ultimate fall dress." Up top, the collared neckline, buttoned front and structured sleeves translate into corporate-core look that's fit for the office. 

A long-sleeve mini is an instant shortcut to a fall-night-out outfit, especially when paired with tall boots and a chic shoulder bag. Another "gently worn" item from Nuuly that's final sale, we can easily see this festive frock at Thanksgiving dinner or holiday parties just as well. 

This pre-loved Nuuly Resale piece is a great find from a crowd-loved brand, now under $20. This animal print dress is perfect for fall trends, just style it with a strong blazer and chunky loafers for a look that says "I'm ready for back-to-work season."