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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:

 

 

how-to-wear-a-shirt-dress

Nic+Zoe Denim Shirt Dress

 

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.

 

how-to-wear-a-shirt-dress

Dress | Hat | Sneakers

 

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!

 

Take a look at how we style a denim sleeveless shirtdress on a beach vacation!

 

 

More Recommended Relaxed Shirt Dresses

 

 

how-to-wear-a-shirt-dress

J.Crew Relaxed-Fit Linen Shirtdress

 

J. Crew 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 super comfy, and the linen is breathable and perfect for sweltering summer days! Available in a range of colors, in sizes XXS-3X, petite sizes XXS-L, and tall sizes XS-XL.

 

 

how-to-wear-a-shirt-dress

Karen Kane Linen Shirtdress

 

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.

 

 

how-to-wear-a-shirt-dress

Caslon Shirtdress

 

Caslon Short Sleeve Shirtdress

 

Readers love Caslon’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 1X-3X, and it’s also available in standard sizes XXS-XXL

 

Take a look at how we style a denim sleeveless shirtdress on a beach vacation!

 

 

how-to-wear-a-shirt-dress

Romwe Striped Cotton Shirtdress

 

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.

 

 

how-to-wear-a-shirt-dress

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.

 

Use packing cubes to pack your dresses and save space in your suitcase!

 

 

More Recommended Romantic Shirt Dresses

 

 

how-to-wear-a-shirt-dress

Karen Kane Chambray Dress

 

Karen Kane Chambray Shirtdress

 

This Karen Kane chambray dress has the classic shirtdress look, but the cinched waist and flowy bottom give it a romantic feel! The long sleeves can be rolled up, and the waist is adjustable for a comfy fit. 

The pretty blue 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.

 

 

how-to-wear-a-shirt-dress

Foxcroft Vienna Shirtdress

 

Foxcroft Vienna Cotton Shirtdress

 

This cotton shirtdress from Foxcroft has a fun dotted print, a flowy skirt, and a bit of a retro feel to it! It buttons all the way down and ties at the waist, creating a nice shape. 

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! Sizes range from 2-18.

 

 

how-to-wear-a-shirt-dress

Halogen Eyelet Sleeveless Cotton Shirtdress

 

Halogen Eyelet Shirtdress

 

Halogen’s sleeveless dress is a flirty take on the shirtdress, with pretty eyelet fabric and a delicate tie at the waist to emphasize curves. It’s sweet and feminine, and the breathable cotton fabric means cool and comfortable, too! 

Sizes range from XXS-XXL

 

Use packing cubes to pack your dresses and save space in your suitcase!

 

 

how-to-wear-a-shirt-dress

Nordstrom Long-Sleeve Shirt Dress

 

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!

 

 

how-to-wear-a-shirt-dress

Dress | Necklace | Mule

 

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!

 

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

 

 

More Recommended Tailored Shirt Dresses

 

 

how-to-wear-a-shirt-dress

Caslon Blend shirtdress

 

Caslon Linen Blend 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 businessy or beachy! 

The fabric is breathable and feels great against the skin. The adjustable tie-waist adds dimension and ties in a pretty bow! It comes in sizes XXS-L, and is also available in navy blue!

 

 

how-to-wear-a-shirt-dress

Nordstrom Pleated Midi Shirtdress

 

Nordstrom Long Sleeve Shirtdress

 

This black, pleated shirtdress from Nordstrom is perfectly loose, hits right below the knee for that fashionable midi length, and has breezy slits at the bottom and on the three-quarter sleeves. Black is flattering, always chic, and incredibly versatile, so you can’t go wrong here! 

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

 

 

how-to-wear-a-shirt-dress

Karen Kane Long Sleeve Shirt dress

 

Karen Kane Stripe Long Sleeve Shirt Dress

 

Karen Kane’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 cotton blend fabric feels nice and soft, and you can roll the sleeves up or keep them long. Sizes range from XS-XL. And check out this dress in a similar striped option, here!

 

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

 

 

how-to-wear-a-shirt-dress

Kilig Sleeveless Casual Dress

 

Beach

 

Some shirt dresses are casual enough to use as a beach coverup, but also look great away from the sand!

 

 

how-to-wear-a-shirt-dress

Dress | Hat | Sandals

 

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 our favorite sandals for travel!

 

 

More Recommended Beach Shirt Dresses

 

 

how-to-wear-a-shirt-dress

Cloth and Stone Striped Button Down Dress

 

Cloth And Stone Stripe Button Down Dress

 

This Cloth and Stone striped button down dress is so lovely! The textured, cotton-blend fabric is soft and breathable, and it’s fully lined, giving you full coverage. Wear it open over a bathing suit, and close it up to head to lunch! 

The midi length is fashionable, and makes it versatile, too! It’s such a cute and easy option for your beachy travels! It comes in sizes XS-XL.

 

 

how-to-wear-a-shirt-dress

Cupshe Vintage Mini Sleeveless Dress

 

Cupshe A-Line Shirtdress

 

The a-line cut on this Cupshe 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 great to throw on over a swimsuit, but the collar and buttons give it a put-together and elevated vibe. Sizes range from S-XL.

 

 

how-to-wear-a-shirt-dress

Michael Stars Cotton Shirtdress

 

Michael Stars Striped Linen Shirtdress

 

When it comes to beachy looks, linen is a no-brainer! The Sammie shirtdress from Michael Stars 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 pink is super cute, or grab it in the blue striped version! Sizes range from XS-L

 

Here are our favorite sandals for travel!

 

 

how-to-wear-a-shirt-dress

Sharagano Button Front Pleated Shirt Dress

 

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.

 

 

how-to-wear-a-shirt-dress

Jacket | Dress | Boots

 

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

 

 

how-to-wear-a-shirt-dress

L.L. Bean Signature Chambray Shirt Dress

 

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.

 

 

how-to-wear-a-shirt-dress

Columbia Silver Ridge Novelty Dress

 

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-XXL.

 

 

how-to-wear-a-shirt-dress

Madewell Denim Tie Waist Shirtdress

 

Madewell Tie Waist Shirtdress

 

Madewell’s denim shirtdress is incredibly soft, and is blended with lyocell, making it even more breathable and comfy! 

The tie waist is removable, giving you some styling options. Plus, denim goes with everything, so it’s 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 00-14.

 

 

how-to-wear-a-shirt-dress

Allegra K Button Up Shirtdress

 

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.

 

 

how-to-wear-a-shirt-dress

Dress | Sandals | Earrings

 

A gladiator sandal in an animal print and chunky earrings keep this outfit from looking too undone.

 

 

More Recommended Boxy Shirt Dresses

 

 

how-to-wear-a-shirt-dress

Eileen Fisher Band Collar Sleeveless Organic Linen Shirtdress

 

Eileen Fisher Sleeveless Organic Linen Shirtdress

 

Cute and casual, this Eileen Fisher sleeveless shirt dress is made of 100% organic linen to keep you cool and comfortable all summer. The band collar and gingham print give it a nostalgic feel. It also features a trendy midi length and handy side pockets!

It’s a perfect dress to pair with comfy walking sandals on a summer sightseeing day! Available in sizes XXS-XL, and plus sizes 1X-3X. It also comes in a pretty aqua blue in plus sizes 1X-3X.

 

 

how-to-wear-a-shirt-dress

Z Supply James Striped Dress

 

Z Supply James Striped Shirt Dress 

 

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

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

 

 

how-to-wear-a-shirt-dress

INDYEVA Frivol Dress

 

INDYEVA Frivol Shirt Dress

 

The Indyeva Frivol shirt dress is really pretty, yet so easy-going. Just throw it on with virtually any shoe option, and you’ll be effortlessly stylish! It’s a simple take on this old classic–it doesn’t have buttons or a tie waist, though it still has all the class!

It’s lightweight, breathable, and super comfy, too! Sizes range from XS-XL.

 

Here are more lace-up sandals we’re in love with this season!

 

 

Womens Shirtdress Product Comparison Chart

 

BRAND | MODEL FEATURES | REVIEWS RATING | PRICE
More Recommended Relaxed Shirt Dresses
J.Crew Relaxed-Fit 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. Check Price
Karen Kane Linen Shirtdress 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!  Check Price
Caslon Shirtdress Readers love Caslon’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.  Check Price
More Recommended Romantic Shirt Dresses
Karen Kane Chambray Dress This Karen Kane chambray dress has the classic shirtdress look, but the cinched waist and flowy buttom give it a romantic feel! The long sleeves can be rolled up, and the waist is adjustable for a comfy fit.  Check Price
Foxcroft Vienna Shirtdress This cotton shirtdress from Foxcroft has a fun dotted print, a flowy skirt, and a bit of a retro feel to it! It buttons all the way down and ties at the waist, creating a nice shape.  Check Price
Halogen Eyelet Sleeveless Cotton Shirtdress Halogen’s sleeveless dress is a flirty take on the shirtdress, with pretty eyelet fabric and a delicate tie at the waist to emphasize curves. It’s sweet and feminine, and the breathable cotton fabric means cool and comfortable, too!  Check Price
More Recommended Tailored Shirt Dresses
Caslon Blend 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 businessy or beachy!  Check Price
Nordstrom Pleated Midi Shirtdress This black, pleated shirtdress from Nordstrom is perfectly loose, hits right below the knee for that fashionable midi length, and has breezy slits at the bottom and on the three-quarter sleeves. Check Price
Karen Kane Long Sleeve Shirt dress Karen Kane’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!  Check Price
More Recommended Beach Shirt Dresses
Cloth and Stone Striped Button Down Dress This Cloth and Stone striped button down dress is so lovely! The textured, cotton-blend fabric is soft and breathable, and it’s fully lined, giving you full coverage. Wear it open over a bathing suit, and close it up to head to lunch!  Check Price
Cupshe Vintage Mini Sleeveless Dress The a-line cut on this Cupshe shirt dress makes it so cute and feminine, while the airy cotton is a dream for hot and humid days!  Check Price
Michael Stars Cotton Shirtdress When it comes to beachy looks, linen is a no-brainer! The Sammie shirtdress from Michael Stars 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!  Check Price
More Recommended Classic Shirt Dresses
L.L. Bean Signature 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.  Check Price
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.  Check Price
Madewell Denim Tie Waist Shirtdress Madewell’s denim shirtdress is incredibly soft, and is blended with lyocell, making it even more breathable and comfy!  Check Price
More Recommended Boxy Shirt Dresses
Eileen Fisher Band Collar Sleeveless Organic Linen Shirtdress Cute and casual, this Eileen Fisher sleeveless shirt dress is made of 100% organic linen to keep you cool and comfortable all summer. The band collar and gingham print give it a nostalgic feel. It also features a trendy midi length and handy side pockets! Check Price
Z Supply James Striped Dress Short and loose, this adorable striped shirt dress has a classic menswear look, with a longer shirttail hem at the back and oversized short sleeves. It can be worn casually with sneakers or spiced up with a belt and chunky sandals!  Check Price
INDYEVA Frivol Dress The Indyeva Frivol shirt dress is really pretty, yet so easy-going. Just throw it on with virtually any shoe option, and you’ll be effortlessly stylish! It’s a simple take on this old classic–it doesn’t have buttons or a tie waist, though it still has all the class! Check Price

 

 


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:

 


 

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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.