10 Transitional Dresses That’ll Carry You from Summer to Fall
Cute, comfy, and perfect for layering, these pieces are made for those in-between days.
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When the calendar says fall but the weather says summer, it can be really tough to pick out an outfit, especially if you’ll be out and about for hours at a time. During those in-between days, the mornings and evenings might seem crisp enough to throw on your favorite fall sweaters and jeans, but by the time the afternoon arrives, it’s probably way too hot for heavy layers. At the same time, though, with autumn on the horizon, your vibrant dresses and flip-flops may start feeling a little too summery.
If you aren’t exactly sure what to wear during the shift in seasons, these transitional dresses are the perfect thing! Each one bridges the gap between summer and fall, thanks to lightweight fabrics, longer hemlines, versatile sleeves, and rich colors and prints. Have you seen Ree Drummond’s cover look for The Pioneer Woman Magazine fall issue this year? She’s wearing The Printed Tiered Puff Sleeve Dress in a pretty olive green and you can dress it up or down depending on the day! When the weather is warm, you can easily wear a dress with stylish sandals or wedges, but once the temperatures start to dip, they’ll look especially chic with ankle boots and outerwear like Alex Drummond’s favorite denim jacket or over-the-knee boots and a cozy shawl. Cute, comfortable, and great for layering, these transitional dresses have you covered when summer starts to fade and fall is waiting to make its grand entrance.
Get your fall wardrobe ready with these ideas:
This denim dress from Ree’s QVC collection is lightweight and movable, so you’ll keep cool when the weather heats up, but the quarter-length sleeves and long hemline will give you just enough coverage for later on in the season. Not to mention, denim is so versatile for fall!
The lace trim, ruched detailing, and ribbon-tied neckline on this dress makes it feel unmistakably summery, yet the chocolate brown hue gives it a fall-inspired edge. During those crisp mornings and evenings, you can sport a light cardigan and sandals in early September or a leather jacket and boots when October arrives.
Alex loves this dress in white for the warmer months; in the fall, a deep red print will get you ready for cozy season. Aside from the dazzling pattern of this gown, the flutter sleeves, cinched waist, and tiered skirt keep this piece from feeling too heavy. Strap on beige sandals for warmer days and zip up brown suede boots at the tail end of the season.
If it’s too hot to break out your cable-knit sweaters, slipping on this cream-colored sweater dress is the perfect happy medium. You’ll get the cozy look and feel of fall fashion without heating up under heavy knit layers. Pair this transitional dress with wedges in the early days of autumn and a denim jacket and boots when the temperature starts to dip.
If you want to bring some fall color to your transitional wardrobe, sage green is a striking choice for the season. While the longer sleeves and maxi length of this summer-to-fall dress gracefully usher in autumn, the cotton fabric won’t weigh you down during those warmer stretches.
One of Alex’s favorite brands, Hill House Home is known for their signature Nap Dress, which traditionally comes in summery colors and prints. But this subtle floral pattern in a dark brown shade will seamlessly mark the shift from summer to fall without leaning one way or the other. The dress is long enough to keep your legs warm, but the sleeves are short enough to feel the breeze.
If you love the look of a sweater dress, but you aren’t too keen on sweating through itchy wool, settle on this chic transitional dress. The light gray hue and knitted print will look gorgeous with a burgundy jacket swung over your shoulders. Regardless of the temperature outside, the scoop neck, drop waist, and pleated skirt are super flattering.
For something that’s sophisticated and comfortable, try this navy shirt dress. The pleats give it that pristinely tailored look, while the pockets offer a practical touch. Whether you don this summer-to-fall gown to a family brunch, a work dinner, or a coffee date with friends, it’ll look elegant and fitting for the season.
With rich colors and moody blooms, this transitional dress from Ree’s clothing line proves that a floral dress isn’t just for the warmer months. The bouncy puff sleeves and tiered tea-length skirt keep things fresh, while the black, mauve, and sage green tones give it an autumnal flair. This getup even works for a semi-formal wedding—if the forecast is brisk, just throw on a shawl!
Plaid is the ultimate fall print, but when the days are still a tad too warm, a heavy flannel probably isn’t the move. Rest assured, you can still rock the autumnal pattern during those in-between days, but a mini plaid dress with a denim jacket is much more suitable for the changing forecast. To take things up a notch, sport brown suede boots and a matching handbag.
Lilly Blomquist is the associate editor at The Pioneer Woman, where she writes lifestyle stories across a wide range of topics—including news, entertainment, holidays, food, and more.
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