One of the trickiest times to get dressed is that stretch between summer and fall. Your white sundresses and bright tropical prints suddenly feel a little too summery, but it’s much too hot for sweaters and boots.

That’s when a good summer-to-fall dress comes in handy. I look for lightweight dresses with short sleeves, richer colors, and darker prints that feel like fall but won’t have you melting in the September heat. Here are some of the best transitional dresses I’ve found for wearing now and well into fall.

What Makes a Good Summer-to-Fall Dress?

The trick is to look for a dress that feels like fall without actually being too warm to wear. I don’t want a heavy knit dress when it’s 80 degrees outside!

Color is a great place to start. Chocolate brown is huge for Fall 2026, along with burgundy, navy, olive, deep red, and other rich shades. Dark florals, animal prints, denim, and subtle plaids also have that fall feeling we’re after.

Short sleeves are especially handy this time of year. You get a little more coverage than a sleeveless summer dress, but you’re not committed to long sleeves when it’s still hot. Lightweight midi and shirtdresses are also some of my favorites because you can change the shoes and accessories as the season moves along.

Best Summer to Fall Dresses for 2026

Here are some of the prettiest early-fall dresses I’ve spotted this year, along with why I think they work so well during this in-between time.

Shirtdresses

A shirtdress is one of my favorite styles for this in-between time of year. It has a little more coverage than a sundress, but it’s still cool and comfortable when the temperatures haven’t caught up with the calendar.

This Print Midi Shirtdress is a great example. The short sleeves keep it cool, while the deeper print feels just right heading into fall. I also love the longer midi length, which makes it easy to wear with sandals now and ballet flats or loafers later.

There’s also the Ann Taylor Classic Sleeveless Collared Midi Shirtdress. Don’t let the sleeveless style fool you. The dark chocolate brown gives it plenty of fall flavor, making this a great choice if you live somewhere that’s hot well into September.

Dark Floral Dresses

You don’t have to give up florals when summer ends. Just switch from bright, tropical-looking blooms to deeper, moodier prints.

The Jardin Embroidered Shift Dress is a fun way to carry green into fall. The deep green color feels right for the new season, while the white embroidery keeps it light enough to wear now. Add sandals while it’s warm, then switch to ballet flats or loafers as you get further into fall.

The CeCe Tie Waist Long Sleeve Shirtdress is another pretty way to wear florals into fall. I love the deep mahogany background because it gives the floral print a richer, more seasonal look. The fabric is lightweight and unlined, so even with the long sleeves, this is one you can start wearing before the really cool weather arrives.

Animal Print Dresses

I’ve always thought of animal print as a neutral, especially once fall rolls around. Browns, camel, black, and tan are already fall colors, so there’s really nothing you need to do to make an animal print dress feel seasonal.

Prefer something shorter? The Talbots Twill Shift Dress in Modern Leopard has an easy shift shape and a softer leopard print. Add a simple brown bag and flats, and you’re ready to go.

The Animal Print Collared Midi Shirtdress is one of my favorites here. It’s feminine, easy to wear, and the short sleeves make sense when the weather hasn’t cooled down yet.

Denim Dresses

A denim dress is such an easy way to start easing into fall. You get that darker, more casual fall look without having to put on a pair of jeans when it’s still hot outside.

I love this Chico’s Denim Faux Suede Detail Dress because it has a little bit of fall built right in. The faux-suede trim gives the denim a richer look and ties in perfectly with all the suede we’re seeing for Fall 2026.

The Weekend Collared Mini Dress in Denim is a cute, sportier option. The short sleeves and easy shape make it perfect for those warm late-summer days. Wear it with sandals or sneakers now, then switch to loafers or ballet flats when the weather cools down.

Easy Jersey Dresses

Don’t overlook a simple jersey dress for this time of year. Jersey is soft, comfortable, and not too heavy, so it works especially well on those warm days when you’re ready to look like fall, but the weather says otherwise.

The Tuckernuck Jersey Lisette Midi Dress in Navy is one of those simple dresses you can do a lot with. Wear it with sandals and a summery bag now. Later, add a chocolate brown bag and a pair of flats or loafers.

I also like the Boden Jasmine Ruched Jersey Dress. The rich brown floral has a much more autumn feel, and the ruching is a nice, figure-flattering touch. It’s an easy way to wear a fall print without jumping into heavier fall fabrics too soon.

More Summer to Fall Dresses to Shop

Still looking for the perfect dress to take you from late summer into fall? Here are a few more summer-to-fall dresses I’m loving right now, with rich colors, pretty prints, and easy styles that work well for this in-between time of year.

3 Easy Ways to Make a Dress Feel More Like Fall

You don’t need to wait for sweater weather to give your dresses a fall update. A few little changes can take a dress you’re wearing now right into the new season.

1. Bring in a little texture. Suede is everywhere again this fall, so this is an easy one. A suede bag, a woven leather belt, or even a chocolate-brown handbag can make a summery dress feel more seasonal without changing the whole outfit.
2. Start with your shoes. Swap summer sandals for sleek loafers, ballet flats, slingbacks, or low-profile sneakers. Chocolate brown and burgundy are especially big for Fall 2026 and instantly give a lighter dress a richer look.
3. Add an updated layer. Once it cools down, try a cropped trench, suede jacket, barn jacket, or a relaxed blazer. These feel fresher for 2026 and are light enough to wear during those in-between weeks.

When Can You Start Wearing Fall Dresses?

You don’t have to wait until the official first day of fall. I start thinking about fall colors toward the end of August, even when the temperatures still feel like summer.

The secret is to dress for the temperature but use the colors of the coming season. A lightweight chocolate brown shirtdress makes much more sense on an 80-degree September day than trying to wear a sweater dress just because you’re ready for fall.

That’s really what transitional dressing is all about. Instead of trying to turn every white sundress in your closet into a fall outfit, add a couple of dresses that naturally bridge the gap. You’ll get more wear out of them now, and they’ll carry you right through those first beautiful weeks of fall.

More Fall Dress Inspiration

Once the weather really does cool down, you can trade these lightweight styles for cozy fall sweater dresses. I’ve rounded up some of my favorites, along with easy ways to wear them without looking bulky.

If you’re always on the hunt for a dress that fits and flatters, take a look at my guide to the best dresses for women over 40. There are lots of great ideas for finding the right style for your shape and lifestyle.