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If I had to narrow down my travel wardrobe to just one dress, it would probably be a shirt dress. It’s the most versatile, comfortable, easy-to-wear outfit for travel. Find out why as I show you how to wear a shirt dress on vacation!
How to Wear a Shirt Dress
Written by: Niki Landry
Table Of Contents
I have more shirt dresses in my closet than I care to admit, and one almost always makes it into my luggage. (A denim one is currently in my bag.) This is a wardrobe staple; I’ve styled a few options to show you how to wear a shirt dress for your next trip:
luvamia Denim Babydoll Dress | Sizes XS-XXL
Relaxed
Give your favorite pair of jeans a break by bringing along a relaxed-fit shirt dress on your vacation, like the denim shirt dress above! Casual and comfortable, a button-down dress will work with sneakers or sandals for an easy outfit.
For dressier occasions, cinch the waist with a belt and add some stylish block heels. You can also wear them with tights on cold days or roll up the sleeves for a laid-back look. There are so many options for one simple dress!
This is our essential list of the best travel clothing brands for women!
More Recommended Relaxed Shirt Dresses
Shop Sizes XS-XL: Tommy Bahama
Tommy Bahama Linen Shirtdress
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-XL.
Shop Sizes XS-XL: Nordstrom
Karen Kane Long Sleeve Linen Shirtdress
Another breezy linen option, this Karen Kane 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 XS-XL.
Shop Sizes XS-XL: Michael Stars | Nordstrom
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!
Nordstrom Striped Shirtdress | Sizes XXS-XXL
Romantic
Packing for your honeymoon, hitting the Mediterranean, or just wanting to look incredibly chic on your next trip? Then this outfit is for you.
Hat | Dress | Bangle | Sandals
A shirt dress in a beautiful bright color is perfect for the summer. The romantic silhouette is fitted at the smallest part of the waist and has a full skirt for a classic and flattering cut. I’ve styled it with scalloped sandals, simple jewelry, and a white panama hat.
More Recommended Romantic Shirt Dresses
Shop Sizes XS-XL: Quince
Quince Chambray Shirtdress
This Quince chambray 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 XS-XXL: Nordstrom
Caslon Gauze Cotton Shirtdress
This cotton shirtdress from Caslon is a midi style with a longline fit! It buttons all the way down and has side slits, creating a nice feminine shape on the wearer.
This dress is made from 100% 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 XS-XXL.
Shop J.Crew: XXS-3X Regular Sizes | XXS-L Petite Sizes | XS-XL Tall Sizes
J.Crew Plus Size Shirtdress
J.Crew short sleeve 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 XXS-3X, petite XXS-L, and tall XS-XL.
Anthropologie Soren Long Sleeve Shirt Dress | Sizes XXS-XL
Tailored
The white button-down shirt is a classic piece that every woman should own. Translated into a dress, it becomes a tailored, all-in-one outfit!
I’ve paired it with on-trend slip-on black shoes to continue the menswear-inspired look and topped it with a multi-strand necklace to add shine and texture. This type of dress would also look great with a belt at the waist and/or strappy sandals.
This outfit would work well for trips to large cities, visiting museums, or enjoying lunch with a friend. This is how to wear a shirt dress – fashion blogger style!
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: Nordstrom | Tommy Bahama
Tommy Bahama Linen Shirtdress
This tailored shirtdress is too chic for words, and will easily become a staple in your travel wardrobe, no matter the destination! It’s super versatile–it can go for a businessy or beachy look!
The fabric is breathable and feels great against the skin.
It comes in sizes XS-XL!
Shop Sizes XS-XL: Quince
Quince Long Sleeve 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.
Shop Loft: XXS-XXL Regular & Petite Sizes
Loft Stripe Long Sleeve Shirt Dress
Loft’s 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 XXS-XXL in regular & petite.
Shirt Dresses are the perfect muti-purpose item to add to your functional travel capsule wardrobe. Learn more in my guide!
Lands’ End Sleeveless Eyelet Shirt Dress
Sizes 2-18 Regular & Petite | 16W-26W Plus
Beach
Some shirt dresses are casual enough to use as a beach coverup, but also look great away from the sand!
This split-neck, tie-waist dress in a bold blue would be a great addition to your tropical destination travel wardrobe. I paired it with strappy slides and a hat for added style and sun protection.
Here are the best sandals for women that love to explore at home or abroad!
More Recommended Beach Shirt Dresses
Shop Sizes S-XXL: Amazon
Herseas Button Down Shirtdress
This Herseas midi button down dress is so lovely! The textured, nylon-blend fabric is soft, light, and moisture-wicking.
The midi length is fashionable, and makes it versatile, too! Wear it open over a bathing suit, and close it up to head to lunch. It’s such a cute and easy option for your beachy travels!
It comes in sizes S-XXL.
Shop Sizes XXS-XL: Carve Designs
Carve Designs Tiered Shirtdress
The flowy, tiered 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.
Shop Sizes XXS-XXL: Faherty
Faherty Striped Linen Shirtdress
When it comes to beachy looks, linen is a no-brainer! The Isha shirtdress from Faherty will have you looking effortlessly stylish and put together, even when you throw it on over a swimsuit with flip-flops and head to the pool!
The blue pinstripe is super cute, or grab it in one of the other colors or patterns!
Sizes range from XXS-XXL.
Sharagano Button Front Pleated Shirt Dress | Shop Sizes 4-22
Classic
The classic style shirtdress has you covered for all destinations and all occasions! With a collar, a shorter length (but not too short), handy pockets, and an overall classy and polished look, you’ll be ready to sightsee in style.
This type of dress will become a go-to choice every time you pack your bags. For a low-key look, I paired this navy shirt dress with neutral booties and a denim jacket, but you can easily dress it up with pumps and a blazer for a business look.
This versatile dress is a must-have for any wardrobe!
More Recommended Classic Shirt Dresses
Shop L.L. Bean: XS-XL Regular & Petite Sizes | 1X-3X Plus Sizes
L.L.Bean Chambray Shirt Dress
L.L.Bean’s chambray dress definitely has that classic shirtdress style, with a collar, buttons, and a length that falls right at the knee. It features a flattering tie-waist, but you can also remove the belt altogether for a slouchier, yet still slightly fitted shape.
Users say the fabric is soft and the dress is so comfortable to wear!
Available in sizes XS-XL regular & petite, and 1X-3X plus.
Shop Sizes XS-3X: Amazon
Columbia Silver Ridge Novelty Dress
Columbia has combined the sophistication of a shirtdress with super functional features for your outdoor adventures! This sporty shirt dress has UPF 40+ sun protection, roll-up sleeves, and functional pockets.
It’s also moisture-wicking, so you can get super active in this cute dress! It’s lightweight and easy to pack, too! Sizes range from XS-3X.
Shop Macy’s: 0-18 Regular Sizes
Lauren Ralph Lauren Tie Waist Shirtdress
Made of 100% cotton, this Lauren Ralph Lauren shirtdress is incredibly soft and comfy!
It has a stylish self-tie waist and the midi length is chic, while the neutral color will go with everything, making it an easy, versatile option for travel! Whether you’re rocking sneakers or wedges, this dress will be a go-to, year-round!
Available in sizes 0-18.
Allegra K Button Up Shirtdress | Sizes XS-XL
Boxy
Look for a loose-fitting, boxy-cut shirt dress for a fresh take on the style. You can go beltless for an effortless look, or get creative with belt placement. Wear a belt lower on the hips or loose with draping fabric to easily change up your outfit.
A gladiator sandal in an animal print and chunky earrings keep this outfit from looking too undone.
More Recommended Boxy Shirt Dresses
Shop Sizes XS-XL: Quince
Quince Stretch Silk Shirtdress
Cute and casual, this Quince long sleeve shirt dress is made of silk to keep you cool and comfortable all summer. It has a relaxed fit, while the band collar and sleek material give it a feminine and elegant feel. It hits just below the knees with breezy side slits.
It’s a perfect dress to pair with comfy walking sandals on a summer sightseeing day!
Available in sizes XS-XL.
Shop Sizes XS-XL: Quince
Quince Linen Shirt Dress
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 S-XXL: Amazon
Zilcremo Short Sleeve Shirt Dress
This Zilcremo shirt dress is really pretty yet so easygoing. Just throw it on with virtually any shoe option, and you’ll be effortlessly stylish! It’s a simple take on the old classic, yet comes with a slimmer fit and cap sleeves, giving it all the class!
It’s lightweight, breathable, and super comfy, too!
Sizes range from S-XXL.
Thigh Society The Cooling Shorts | Sizes XS-6X
Best Shorts to Wear Under Dresses
If your looking for a shorts to wear under your dresses Thigh Society is a reader favorite! The Cooling anti-chafe shorts from ThighSociety are raved about by TFGers for so many reasons, especially their silky, hi-tech performance fabric. These shorts pull heat and moisture away from the body, keeping things cool, fresh, and chafe-free on even the hottest of days.
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 and lengths and range in sizes from XS-6X!
What are your best tips on how to wear a shirt dress? Share your thoughts below!
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.
I love the shirtdress idea! They are classic and fun! I wear my button down one over my leggings and tee shirt- open as a sort of jacket!
I’ve been trying to learn how to wear a shirt dress without looking ridiculous. Thank you! These are beautiful!
I agree. Shirt dresses are my absolute favorite. Thanks for the recommendations. I’m always looking for new ones.
Just packed 2 short dresses for Greece!
What a bunch of really cute styles! xo Loren
Thanks for reading Loren!
I love to pack shirtdresses for my adventures. Do you have any suggestions for wearing them in cooler climates?
Thanks for reading Emily! I’d definitely suggest layers and boots! Leggings may be great for some dresses, depends on the style I suppose! A good jean jacket goes a long way! Thanks again! Happy travels!
This is great! I’ve always struggled with how to wear a shirt dress.
🙂 I hope you’ve got some ideas now!