30 Cute Dresses That'll Work Perfectly for Your Summer-to-Fall Transition

When it comes to outfit dilemmas, a dress is almost always the solution. There's no need to worry about finding matching pants for your top, and since it's one item, all you need to do is throw it on and go. If you want to make things more interesting, there are easy ways to add elements to the look by playing around with accessories or adding a jacket or cardigan. Obviously, the latter is easier to do when the weather isn't blazing hot, which is why our favorite time to wear dresses is when we're transitioning from the summer into the colder weather. It's still the right time for breezy dresses, but there's no harm in layering a blazer over one when the temperature starts to drop. 

There are plenty of A+ dresses on the market, but we've narrowed it down to 29 that we think deserve your attention right now. You can wear the options below with strappy sandals to keep your summer vibe going or even pull on knee-high boots as we transition into the next season.

Next, Color Report: The 7 Shades Everyone Will Be Wearing This Fall

Assistant Market Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.