11 Petite Midi and Maxi Dresses for Summer, From $20

As someone five-feet-tall, I know that shopping for a midi-length or maxi dress that won’t drag on the ground is, well, a drag. Either you have to spend time (and money) tailoring it, or do some legwork to find stylish petite options from online retailers, considering the right size is rarely in stores. With a few summer vacations on my calendar, I opted for the latter option and browsed through my go-to petite brands to find flattering dresses that fit my frame perfectly. 

Naturally, I had to share my findings with my fellow petite shoppers, so I rounded up the best maxi and midi dress options from Amazon, J.Crew, Nordstrom, Anthropologie, and more. From a $29 travel-friendly knit dress to a European-summer-inspired maxi shirt dress, I found styles for every travel itinerary. Keep reading for 11 of my top picks, starting at $20.

Best Overall Petite Dresses

Gap Knit Midi Dress

You’ll never catch me in the airport in a dress above my knees, but now and then, I like to throw on a stylish, comfortable midi dress to elevate my travel look. This Gap ribbed knit option is perfect for exactly that, and with a $29 price tag, I immediately added it to my shopping cart. I opted for the olive green shade, which will seamlessly transition into fall, but it is also available in black, striped, and fuchsia.

Livtany Sleeveless Slim Fit Midi Dress

This sleeveless midi dress is effortlessly chic and looks much more expensive than its $35 price tag. The fitted top is made from a comfortable, smocked knit material, and it’s paired with a puffed peplum skirt featuring a flattering drop waistline that helps make your torso appear longer—perfect for petite shoppers.

Quince Cotton Mixed Media Tank Dress

Quince is known for its effortless travel clothing, and this midi tank dress is no exception. The travel-ready piece is made from a breathable, soft cotton blend. One five-foot-two reviewer wrote that “the dress is perfect,” adding that it’s “simple and sophisticated.”

Gap Lace-trim Tiered Maxi Dress

This light and airy maxi dress captures the art of summer dressing. It is trimmed with lace detailing and features an embroidered design on the bodice. Now, the hard part is deciding between the classic black shade and the cottagecore-inspired indigo. Considering they’re both on sale, I might have to snag both! 

Fisoew Spaghetti Strap Dress

While this midi dress isn’t available in petite sizing, it has adjustable spaghetti straps that allow for a customizable fit. The fit-and-flare dress, which can be easily dressed up or down, features a fitted ribbed bodice with a low scoop back and a flowing skirt. 

Anrabess Summer Casual Maxi Dress

This maxi dress features a similar design to the above option, with a fitted, tank top bodice and an airy skirt, but its high neckline provides a bit more coverage. One five-foot-tall reviewer wrote that it’s a “great length,” and added that they “loved it so much,” they bought a second color. The best part? It’s marked down to just $22 right now, so I’m not missing my opportunity to shop it while it’s on sale.

Lands’ End Cotton Voile V-neck Tie Strap Maxi Dress

This Lands’ End petite maxi dress is begging to be worn on a tropical vacation, and its airy, lightweight material will help keep you cool on a hot summer day. It features a stretchy, smocked elastic back and adjustable tie straps, providing additional length customization for the petite dress.  

J.Crew Petite Cerise Shirtdress

I’m not headed to Europe this summer, but if I were, I could easily picture myself strolling the cobblestone streets of Paris in this top-rated breezy shirtdress from J.Crew. The shirred elastic waist provides shape to the flowy silhouette, and it comes with a slip lining underneath the subtly sheer overlay fabric.     

Loveappella V-Neck Jersey Maxi Dress

I can already tell this ultra-comfy jersey maxi dress would become one of my staple travel pieces. It features flattering details, such as a smoothing waistband and a deep V-neck. Plus, the pullover design makes it easy to throw on and go, whether I’m catching an early morning flight or making a quick change before dinner.

Exquise The Tobie Shirt Dress

I can’t resist a perfectly tailored dress, and this petite Anthropologie number fits the bill. The casual yet elegant shirt dress features eye-catching details, including a classic collar, exaggerated sleeves, and flattering pleats around the bodice. Additionally, the button-up front allows for a customizable look that can be worn as a dress or paired over a pair of shorts and a classic white tee. 

J.Crew Petite Cap-Sleeve Midi Dress

This top-rated J.Crew midi dress is made from a summery, lightweight linen material and has a smocked waistband with a tie at the center and capped sleeves. One reviewer raved that it’s “very flattering and comfortable,” and a five-foot-three shopper wrote that “the length is perfect.” Right now, the midi is an additional 40 percent off, bringing the price down to $84.

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