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If I had to pick just one dress for my travel wardrobe, it would definitely be a shirt dress. It’s the ultimate combination of comfort, versatility, and ease, making it the perfect choice for any vacation. Keep reading as I show you how to style a shirt dress on your next getaway!

 

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How to Wear a Shirt Dress

Written by: Niki Landry

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Table Of Contents

 

I’ll admit, I have more shirt dresses than I probably need, but one is always packed in my luggage (currently, it’s a denim one!). This wardrobe essential is a travel must-have, and I’ve styled a few favorites to show you just how versatile it can be for your next trip.

When it comes to packing light and staying stylish on vacation, a shirt dress is a game changer. It’s comfortable, versatile, and easy to dress up or down, making it perfect for any occasion. Here’s how I style a shirt dress for a variety of travel scenarios.

 

 

Sunglasses | Shoes | Shirtdress | Hat | Bag

 

Casual and Relaxed Look

 

A shirt dress is the perfect piece to swap out for your usual jeans when you want something comfy yet stylish. I love a denim shirt dress for a laid-back vibe. Pair it with sneakers or sandals, and you’re set for a day of sightseeing or lounging. For cooler weather, add a scarf or a light jacket for extra warmth without compromising comfort.

Styling Tip: If you want a more defined waist, simply add a belt. It’s an easy way to elevate a relaxed look while still keeping it casual.

 

This is our essential list of the best travel clothing brands for women!

 

 

More Recommended Relaxed Shirt Dresses

 

 

Madewell Boxy Short Sleeve Denim Shirtdress | Sizes XXS-XXL

 

Madewell Boxy Denim Shirtdress

 

This Boxy Short Sleeve Denim Shirtdress from Madewell offers a relaxed and effortlessly chic look for any occasion. Featuring a comfortable, loose fit, this denim dress is designed with short sleeves and a button-down front, making it perfect for warm weather.

Its versatile design pairs well with sneakers for a casual day out or can be dressed up with accessories for a more polished look. The soft denim fabric ensures comfort, while the boxy silhouette gives it a laid-back, modern vibe, making it a staple piece for your wardrobe. Available in sizes XXS-XXL.

 

 

Shop Sizes XS-XL: Quince

 

Quince Chambray Shirtdress

 

This Quince chambray shirt dress has a classic shirtdress look, comfortable and flowy bringing out a romantic feel! The long sleeves add more versatility, and is adjustable for a comfy fit.

The pretty washed black color is versatile, too. This dress would look great as a daytime outfit or dressed up for a night out! Available in sizes XS-XL.

 

 

Shop Sizes XXS-XXL: Nordstrom

 

Caslon Belted Shirtdress

 

This belted chambray shirtdress from Caslon combines classic style with modern comfort. Made from soft chambray fabric, this dress features a button-down front and a flattering belted waist that accentuates your silhouette. The long sleeves can be rolled up for a more relaxed look, while the versatile design makes it perfect for both casual outings and more polished occasions.

Its timeless chambray fabric adds a laid-back vibe, while the belt adds definition for a chic, feminine shape. Pair with sandals or sneakers for a stylish yet comfortable outfit. Grab them in sizes XXS-XXL.

 

 

Hat | Sandals | Shirtdress | Sunglasses | Bag

 

Romantic Getaway Ready

 

Heading to a romantic destination? A shirt dress in a soft, feminine fabric like cotton or linen is perfect for those dreamy days. Opt for one with a cinched waist and a full skirt, which creates a flattering silhouette. I love pairing this style with simple jewelry, a hat, and sandals for a look that’s both effortless and chic.

Styling Tip: Add a colorful scarf or statement necklace to dress it up for an evening stroll or dinner date.

 

 

More Recommended Romantic Shirt Dresses

 

 

Shop Sizes XS-3XL: Land’s End

 

Land’s End Linen Shirtdress with Belt

 

This linen shirtdress manages to look both laid-back and polished at the same time! It’s a simple piece that’s effortlessly stylish. Just throw on a cute pair of sandals or slip on sneakers and some simple accessories, and you’re good to go! 

The relaxed fit makes it very comfy, and the linen is breathable and perfect for the sweltering summer days! Available in a range of colors, and in sizes XS-3XL.

 

 

Shop Sizes XXS-XXL: Nordstrom

 

Caslon Long Sleeve Linen Shirtdress

 

Another breezy striped linen shirtdress option, this Caslon shirtdress gives you an easy, chic outfit for your summer travels. This is the ultimate day-to-night option, as the sleeves can be unrolled when the temps cool down, and it’ll look instantly dressy with a simple shoe change!

It’s lightweight, hits right at the knee, and has a loose yet pretty shape. Sizes range from XXS-XXL.

 

 

Shop Sizes XXS-3XL: Pact

 

Pact Lightweight Cotton Shirtdress

 

This cotton shirtdress from Pact is a midi style with a longline fit! It buttons all the way down and has a pockets creating a nice feminine shape on the wearer.

This tie waist shirtdress is made from 100% organic cotton, so it’ll be light and comfortable enough for warm weather trips! Wearers of all sizes rave about how well this dress fits, and how flattering it is! Available in sizes XXS-3XL.

 

 

Hat | Bag | Shirtdress | Sunglasses | Shoes

 

Tailored and Chic

 

For a more polished look, go for a tailored shirt dress with a structured fit, like a classic white button-down. This option is perfect for city adventures, museum visits, or business-casual outings. Pair it with stylish loafers or block heels and some minimal accessories to keep things sleek and modern.

Styling Tip: Add a belt to accentuate the waist or layer it with a blazer for a more sophisticated look.

 

We have rounded up our favorite convertible travel dresses that will help you pack light and stylishly!

 

 

More Recommended Tailored Shirt Dresses

 

 

Shop Sizes XS-XL: Michael Stars

 

Michael Stars Linen Short Sleeve Shirtdress

 

Readers love Michael Star’s summery pieces! This short sleeve shirtdress is so cute and easy to wear! It’s comfortable, lightweight, takes up little room in your luggage, and is super versatile. 

It’ll look just as stylish at the beach as it will in a big city. You can button it all the way up for a discreet look, or button it lower to show a tank underneath! Sizes range from XS-XL.

 

Take a look at our curated list of dresses that aren’t just pretty, they’ll actually help you stay fresh and cool, too!

 

 

Shop Sizes XS-XL: Quince

 

Quince Long Sleeve Shirtdress

 

Short and loose, this adorable Quince shirt dress has a classic menswear look, with a longer shirttail hem at the back and long sleeves. It can be worn casually with sneakers or spiced up with a belt and chunky sandals! 

The linen fabric means it’s perfect for active days or hot, humid weather!  Available in sizes XS-XL.

 

 

Shop Sizes: XS-4XL: Old Navy

 

Old Navy Plus Size Shirtdress

 

Old Navy short sleeve shirt dress is a flirty take on the shirtdress, with sleek fabric and a delicate tie at the waist to emphasize curves. It’s pretty and feminine, and the lightweight fabric means cool and comfortable, too! 

Sizes range from XS-4X.

 

 

Hat | Tote | Shirtdress | Sunglasses | Sandals

 

Beach to Street Style

 

Some shirt dresses are versatile enough to double as a beach cover-up or a casual day dress. A lightweight, flowy shirt dress in a breezy fabric like linen is perfect for throwing over a swimsuit at the beach. Afterward, pair it with strappy sandals, a sun hat, and sunglasses for a chic post-beach look.

Styling Tip: For added flair, layer with a crossbody bag or a floppy hat to complete the vacation vibe.

 

 

More Recommended Beach Shirt Dresses

 

 

Shop Sizes XXS-3XL: J.Crew

 

J.Crew Linen Shirt Dress

 

The relaxed beach shirt dress from J.Crew  is the perfect addition to your warm-weather wardrobe. Made with a breathable linen-cotton blend, this shirt is lightweight and comfortable, making it ideal for beach days, casual outings, or layering over swimwear.

The relaxed fit ensures a laid-back, effortless look, while the classic white color makes it a versatile piece that pairs easily with any of your summer essentials. Whether you’re lounging by the pool or strolling along the shore, this shirt offers both style and comfort in one simple piece. It comes in sizes XXS-3XL!

 

 

Shop Sizes XS-XL: Nordstrom

 

Karen Kane Stripe Long Sleeve Shirt Dress

 

Karen Kane striped shirt dress has the crisp look of a classic button-down, all the way down to the sleeves, and a relaxed fit! Contrast the menswear-inspired style with some cute sandals, delicate jewelry, and a crossbody bag for the ultimate stylish, on-the-go outfit! 

The 100% cotton fabric feels nice and soft, and you can roll the sleeves up or keep them long. Sizes range from XS-XL. 

 

 

Shop Sizes XXS-XL: Carve Designs

 

Carve Designs Button Down Shirtdress

 

The flowy, tunic design of this Carve Designs shirt dress makes it so cute and feminine, while the airy cotton is a dream for hot and humid days! 

It’s super cozy and perfect to throw on over a swimsuit, yet its ruffle details and pretty buttons give it a put-together and elevated vibe.  Sizes range from XXS-XL.

 

 

Hat | Backpack | Shirt Dress | Sunglasses | Sneakers

 

Day-to-Night Transition

 

One of the best features of a shirt dress is how easy it is to transition from day to night. A simple classic shirt dress can be dressed up for an evening out by adding accessories like a chunky necklace, some heels, and a clutch. Just switch out your sneakers for a more sophisticated shoe, and you’re good to go!

Styling Tip: Play with sleeve length and roll them up for a more casual day look, or leave them down for a sleek, evening-ready vibe.

 

 

More Recommended Classic Shirt Dresses

 

 

Shop Sizes S-L: Zara

 

Zara Sleeveless Shirt Dress

 

The Piqué Shirt Dress from Zara offers a stylish yet simple design for a variety of occasions. Crafted from a comfortable blend of polyester and elastane, this midi-length dress features a flattering V-neckline and short sleeves. The side draped detail adds a subtle twist to the classic shirt dress silhouette, while the front closure with metallic buttons enhances its modern charm.

Available in black, this versatile piece is perfect for both casual and semi-formal settings, offering a chic, streamlined look that can be dressed up or down with ease. Whether worn with sneakers or heels, this dress is an effortless wardrobe staple. Available in S-L.

 

 

Shop Sizes XS-XL: Quince

 

Quince Silk Shirtdress

 

This silk shirtdress from Quince is perfectly loose, hits above the knee for that breezy, summery length, and is contrasted by long, elegant sleeves. The silk material has a hint of stretch, making it flattering, chic, comfy, and incredibly versatile. Not only that, but the silk fibers are nourishing to the skin, hypo-allergenic, and naturally thermoregulating to help maintain a comfortable body temperature! 

This dress could look cute with black sandals for an edgy summer look, or paired with booties in the fall!  Available in sizes XS-XL.

 

Shirt Dresses are the perfect muti-purpose item to add to your functional travel capsule wardrobe. Learn more in my guide!

 

 

Shop Sizes XXS-3XL: Anthropologie

 

Anthropologie Tiered Shirtdress

 

The Bettina midi button down dress by Maeve from Anthropologie is a stylish and versatile option for any occasion. Crafted from a lightweight fabric, this dress features a relaxed fit with a flattering tiered design. The button-down front adds a classic shirtdress touch, while the tiered silhouette offers a feminine and flowy look.

Its midi length makes it perfect for both casual outings or dressing up for a more polished look. Pair it with sandals or sneakers for daytime activities or dress it up with heels for an evening out. This effortlessly chic dress is a must-have for your wardrobe. It comes in sizes XXS-3XL.

 

 

Thigh Society The Cooling Shorts | Sizes XS-6X

 

Best Shorts to Wear Under Dresses

 

If you’re looking for shorts to wear under your dresses, Thigh Society’s The Cooling Anti-Chafe Shorts are a reader favorite. These shorts pull heat and moisture away from the body, keeping things cool, fresh and chafe-free on even the hottest of days due to their silky hi-tech performance fabric.

They’re tagless, don’t roll or bunch, and are ultra-thin and lightweight yet stretchy and durable as can be. Plus, they come in a wide range of colors, lengths and sizes from XS-6X!

 

 

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What are your best tips on how to wear a shirt dress? Share your thoughts below!

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For more tips on travel fashion, please read these posts:

• Beach Dresses You Can Wear On and Off the Sand 
• Best Vacation Maxi Dresses for Summer
• 5 Sundress Outfits to Transform a Summer Dress
• The Best 2-Piece Dress for Travel

 

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Author Bio: Niki is an interior designer and artist from Louisiana. In addition to her design work, she writes for local and online publications sharing her experiences and passion for travel. Niki is currently adding stamps to her passport while building her design practice, Niki Landry Designs.

 

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