24 of the Best Summer to Fall Dresses You Can Buy Right Now

Plus styling tips on how to take your dresses from summer into fall!

1. Summer Dresses With Flouncy Skirts

Summer Dresses and Flouncy Skirts

Skirts with movement look super cute for all your summer outings. These casual party dresses are the best -- easy, breezy, and fun! You can take the same look back to school with you this fall by adding a chunky sweater. The contrast of a big knit with a twirly bottom is perfection. Add a pair of ankle booties and you’re all set!

2. Spaghetti Strap Dresses

Spaghetti Dresses

No one ever said that fall dresses have to have sleeves. Your summer party dresses with the skinniest of straps can transition into fall really easily! Adding a long-sleeved fitted tee underneath (even a turtleneck!) makes it weather appropriate and totally on trend.

3. Cap Sleeve Dresses

Cap Sleeved Dresses

Speaking of sleeves, the perfect summer to fall transition style is the cap sleeve. It has a fun and flirty look in summer, but won’t leave you freezing when temps drop. This casual fall dress look works for school and the weekend.

4. Maxi Dresses

Summer Maxi Dresses

Maxi dresses are a classic summer look and since choosing summer to fall dresses is all about the right coverage, they’re perfect for back to school too. Look for prints that aren’t too summery (think more muted florals, stripes, or solids) and colors that don’t scream summer-only (no neon!). Then add a jean jacket, and done!

5. Summer Jumpsuits


The same thinking that applies to transitioning maxi dresses to fall applies to jumpsuits too. This look is especially perfect if you don’t love wearing dresses to school and prefer pants. With the addition of a jean jacket or cute little cardigan, you have an ideal look for back to school.

6. Shift Dresses

Summer Shift Dresses

The shift dresses you wear in summer have a shape that’s endlessly workable for fall. There are a couple of ways we like to take this style between seasons. They look great with ankle booties, making them the perfect summer to fall dresses footwear-wise. They also pair well with a hem-length cardigan sweater, which makes a cute, cool-weather appropriate statement.

7. Midi-Length Dresses

Midi Dresses

Not quite a maxi, but still length-appropriate for back-to-school -- midi-length dresses transition between summer and fall perfectly. In warm weather, we love to wear this style with strappy, flat sandals or high wedges. Take the look into fall by pairing the dress with a cute pair of sneakers for a style that’s both girly and sporty.

8. High-Neck Dresses

Summer High-Neck Dresses

Summery dresses with a high neck are already on their way to being appropriate for fall. To take the style between seasons, you have a few options. Add a moto or jean jacket over the dress or pop a fitted tee under the dress. Either look pairs perfectly with this summer- and fall-ready neckline.