12 Transitional Dresses to Buy Now and Wear Into Fall—Plus Styling Tips for Any Weather

We like to get the most out of our wardrobes, so as the summer draws to a close, we’re only interested in shopping for transitional dresses. Meaning, summer dresses we can wear now *and* into the fall with just a few smart style swaps.

The obvious being switching your sandals for closed-toe shoes such as loafers, ballet flats or boots. But not all dress styles fit transitional footwear. And no matter how hard you try, sometimes a multi-colored floral print mini does just look out of place in October.

To help you shop smart, we’ve rounded up the best transitional dress trends—plus our favorite styles worth shopping.

Denim dress

Thanks to the heavyweight fabric, a denim dress will effortlessly see you from summer into fall, requiring few styling substitutions in the process. One of the best ways to wear them is with one of our favorite transitional shoe trends—think fashion sneakers, loafers and socks, or boat shoes. In time, this will become boots, be it biker or cowboy styles. Look for mini-length designs with sleeves to make the most of the lingering sunshine, and when the mercury truly drops, layer a roll-neck underneath for maximum warm layers.

Polka dot dress

Polka dots are still set to be big news this season, as seen on the AW25 runways at Altuzarra, Fendi, and Brandon Maxwell. Brown polka dot patterns will feel really seasonal and give a refreshed take on the print, but black-backed versions are still totally acceptable. Again, look for short-sleeve styles and get ready to swap your sandals for boots. We’re also excited to wear a jumper over the top, belted in place, to create the illusion of a polka dot skirt.

Knit dress

Similar to denim, a knitted dress transitions well for fall thanks to its fabric, which is lightweight enough to wear now with bare legs and sandals. It looks just as good with boots (and tights too, when it gets really cold). Even knitted sleeveless styles, when paired with the right footwear, can work as late as December. Truly, few dresses are more versatile.

Tomato red dress

Pastel colorways are associated with spring and summer, while warmer, earthier tones belong to fall as they evoke the feeling of the changing season. Shelving your butter yellow (*sob*) in favor of a new season color trend is one way to instantly feel more seasonal. Enter: tomato red, per the AW25 runways at Altuzarra, Calvin Klein, and Christopher John Rogers. Admittedly, not your typical fall hue, but that’s exactly what makes it a great buy for now. Let your accessories—swap white for black, and sandals for boots—change the mood come September.

Midi and maxi dresses

Regardless of print, fabric or color, the easiest kind of transitional dress is a maxi or midi dress. Not only does the longer hemline keep your legs warm in the cooler weather of fall, but it also guarantees you can wear your dress with boots (aka our favorite seasonal footwear), as there’s less likely to be an awkward gap between the bottom of your dress and the top of your boots. No matter the boot style you opt for, ideally, you want your dress to finish below the tops of your boots.

Slip dress

Slip dresses have dominated summer dress trends and are set to stay for fall. Good news if you’ve already invested, and giving you the perfect excuse to finally do so if you’ve so far been resisting. Look to the AW25 runways for styling inspo, where Cecilie Bahnsen and Blumarine offset the delicate sheer fabrics with socks and chunky sneakers and knee-high boots, respectively. Similarly, Louis Vuitton relied on dark accessories to bring an fall mood, and Chloé skipped straight to winter, pairing lace negligees with faux fur coats.

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