How to Style a Shirt Dress, According to Stylists

9 Cute Ways to Style a Shirt Dress, According to Stylists

The versatile shirt dress has tons of potential.

Published on July 30, 2024

woman in shirt dress — Photo:
Yelena Shestakova/Getty Images

A shirt dress takes your classic button up dress shirt and lengthens it so it hits anywhere from mid-thigh to right around the ankles. It’s basically the best of both worlds: You get to enjoy the sophistication of a dress but with the breathability and comfort of a shirt.

“The thing I like best about a shirt dress is that you can dress it up or dress it down depending on the look you are going for,” says Chellie Carlson, a wardrobe stylist based in Los Angeles. Available in all sorts of silhouettes and textiles, there are a ton of ways you can style a shirt dress.

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Sneakers and Denim Jacket

For a non-fussy everyday look, Carlson says to style your shirt dress with a cool sneaker, a light denim jacket (or cardigan over your shoulders) and then head out the door. “This pairing is great for comfort while running errands around town,” she says. “A cropped jacket will hit you right at the waist for a better balanced silhouette.”

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Statement Heels and Jewelry

A statement-making kitten or block heel will instantly elevate a shirt dress. Nicole Russo, a New York City-based personal stylist, says this is more unexpected than a sandal, but still tweakable according to your personal styles and walking needs. “The shoes add sartorial depth, but you can still look and feel presentable for any occasion,” she explains. “If wearing a bolder shoe is outside your comfort zone, choose either the dress or the shoes to be your statement piece.” Belting the shirt dress brings the eye to the waist to create a more flattering silhouette.

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Sandals and Straw Tote

Heading to the beach? Throw on a perfectly wrinkled linen shirt dress—either in a neutral or a fun color like this one—and add some strappy sandals. “This look is perfect for a weekend brunch or weekend at the beach,” says Carlson. “It provides breathability in the heat.” Complete it with an oversized straw tote and matching bucket hat.

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Oversize Blazer and Slingbacks

Whether you’re heading to the office or happy hour (maybe from one to the other), a blazer and some slingbacks are the way to go. They “elevate the outfit, allowing it to go from day to night,” Carlson says. “Wear an oversized blazer for a more casual cool vibe, and roll the sleeves to mid-forearm to give it a bit more polish.”

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Pointed Heel and a Belt

Go for an ultra-chic vibe by belting your shirt dress and slipping into some pointed-toe heels. Delicate jewelry and a matching bag bring the look home. Monochromatic neutrals work brilliantly, as seen here, but don’t be afraid to play with some color, too.

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Knee-High Boots and Bag

Here’s another easy, chic fit that allows for some customization—it’s also a great option for cooler fall and spring weather. “Whether western leaning, equestrian, or bohemian and slouchy, your favorite boots are bound to match,” says Russo. She suggests pairing the boots with a brighter, small bag to add some dimension and a little femininity. You could also try an oversized bag that matches the shoes, as pictured here.

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Swimsuit and Flip Flops

Who says you have to style a shirt dress for streetwear? A flowy, oversize option serves as the perfect coverup when heading to the pool or beach. Pull it on over your favorite swimsuit and pair it with flip flops and sunglasses.

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Platform Sandals and Jean Shorts

For a twist on your dress shirt—and a way to keep cool in the summer—unbutton it from the waist down and add a pair of jean shorts. Platform sandals lend a bit of height and style factor, and a matching bag and sunglasses tie it all together.

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Trousers and Tee

Similarly, try styling a shirt dress as a cardigan and add a pair of trousers and simple tee underneath. “It’s unexpected and has the ease of throwing on a dress, but is more creative,” Russo says. She adds, “This look acclimates to different weather and personal styling with various prints, shapes, and colors, too.

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