Part shirt, part dress, and all style! A shirt dress can do not just double duty, but quadruple duty in your wardrobe. So if you’re thinking about how to wear a shirtdress, it’s actually hard to think of a shirt dress outfit you couldn’t wear.

You can wear a shirt dress alone as a dress, obviously. But you can also wear it over trousers, or open as a duster coat. Or you can even wear it as a cover-up at the beach.

In this article, you will find lots of inspiration on how to wear a shirtdress as well as some of the best ways to put together a shirt dress outfit for any occasion.

You’ll also find my favorite shirt dresses in stores now.

how to wear a classic shirtdress |

Melinda (above) wears a very classic shirt dress with statement jewelry.

Check out this similar navy shirtdress, woven straw bag and sandals to steal her look.

How to wear a shirt dress

I can think of few other items that are so versatile that you can wear them to the office, for a casual weekend, for a day at the beach, or for a swish evening out.

But a shirt dress ticks all of those boxes. 

1. Wear your shirtdress on its own

how to wear a white shirtdress |

It goes without saying that you can simply wear your shirtdress on its own.

Sandra (above) opts for a stylish monochrome look, and adds a touch of color with her red lipstick.

Recreate her look with this similar sleeveless shirtdress, sandals, crossbody bag and necklace.

wearing shirtdress with red shoes |

Lucky Brand daisy print shirtdressEarth sandalTreasure & Bond woven straw toteAkola drop earrings

2. Wear over your wide-leg pants

wear a shirtdress over wide-leg pants |

While it can be easier to think about wearing your shirtdress over narrow-leg pants or jeans, wide-leg styles can also look stunning.

Alice (above) adds a retro feel to her outfit with her platform pumps.

Here is a floral shirtdress you can try from Tory Burch that you can pair with these similar wide leg pants, Gucci pumps and shoulder bag.

a striped shirtdress and white jeans |

Club Monaco stripe shirtdressNobody Denim wide leg jeansJeffrey Campbell zip bootie Antik Kraft convertible clutchSterling Forever earrings

For more inspiration, read our article on how to wear tunics or dresses with pants.

3. Wear over your leggings

wearing a striped shirtdress over leggings |

You may prefer to cover up your legs, either because you feel your shirtdress is shorter than you are comfortable with, or because the weather is still a little chilly.

Anita (above) wears her striped midi dress with a warm underlayer. You could get the same look with opaque tights or leggings.

Check out these printed shirt dresses from 1901 and Court & Rowe and match with these similar leggings and booties.

a shirtdress worn with leggings |

Sam Edelman abstract shirt dressZella leggingsFly London sandalAntik Kraft convertible clutchSterling Forever earrings

Read our complete guide on how to wear leggings for women over 40.

4. Wear over your jeans

a shirt dress worn as a topper over jeans |

There are few items of clothing that you can’t wear with your jeans, and a shirt dress is no exception.

Georgette (above) opts for a shirtdress worn open as a duster jacket.

Get her look with this similar shirtdress, jeans, tank top, rattan bag and sandals.

animal print shirtdress and jeans |

Rails leopard print shirtdressMade in Blue skinny jeansJeffrey Campbell zip bootieTreasure & Bond woven straw toteAkola earrings

5. Wear over narrow leg pants

shirtdress worn over narrow pants |

An outfit which is easy to put together, stylish and universally-flattering is a shirt dress worn over narrow or straight-leg pants.

Dayle (above) chooses a fun style giving a pop of blue and yellow.

Get her look with this similar white shirtdress and pants, and wear with a pair of Fly London sandals.

shirt dress and narrow leg pants |

1901 tie waist shirtdressHalogen tie waist twill pantsLouise et Cie sandalNordstrom hobo bagSterling Forever earrings

6. Wear for evening

a shirtdress worn for evening with heels |

Versatile enough to wear for day or night, a shirt dress is also a stunning option to wear for a night out.

Carole (above) chooses animal print and adds allure with the side split.

Check out these zebra printed shirt dresses from Nanushka and City Chic and this similar pair of ankle strap sandals to steal her look.

You could also choose a dress with asymmetry or a high-low style.

high low shirt dress |

Mark + James by Badgley Mischka high/low shirtdressNordstrom shimmer wrapNina open toe pumpNordstrom studded clutchSterling Forever earrings

7. Wear for summer

summer shirtdress outfit |

Easy, breezy and stylish, a shirt dress is a great option to pack if you are heading off on vacation.

You can wear for sightseeing, or pop over your swimsuit after a day at the beach.

Rachel (above) chooses an all-neutral outfit worn with woven accessories.

She is wearing a sold-out shirtdress from Marks & Spencer. You can check out these other shirtdress options from the brand like this floral printed shirtdress or this tiered shirtdress which are both perfect to wear during summer.

Complete her look with this similar straw tote and strappy sandals.

striped shirtdress with white pants for summer |

Court & Rowe tie waist sleeveless shirtdressAnne Klein slim fit pantsVince flat sandalUrban Originals straw toteBrixton felt fedoraAkola earrings

8. Wear as a beach cover-up 

wear a shirtdress over your swimsuit |

Another summer idea for you. If you’ve had a day at the beach or by the pool and want to pop a cover-up on to go to the bar or for lunch, a shirt dress is ideal.

Lizzi (above) looks beautiful in her white dress and summer accessories.

Check out this similar shirtdress, straw hat, tote and flip flops.

a shirtdress as a beach cover-up |

Dolan shirtdressMiraclesuit one-piece swimsuitTory Burch flip flopUrban Originals straw toteAkola drop earrings

See are our top picks of the best one piece bathing suits for women over 40.

9. For a daytime event or wedding 

How to wear a shirtdress: 9 shirt dress outfit ideas for you |

Heading to the office, for lunch with friends or for a summer event? A shirt dress can work wonderfully for absolutely any occasion.

Kim (above) chooses beige worn with animal print.

She is wearing a shirtdress from Modern Citizen that also comes in two other colors. Complete recreating her look with this similar Gucci tote, ankle strap sandals and earrings.

Also, take a look at this article, which asks can you wear beige without looking boring?

satin shirt dress |

Vince silk dressLouise et Cie sandalAntik Kraft convertible clutchADORNIA y-necklaceAkola earrings

You might also like to read our articles on how to dress for weddings in winter and summer.

The best shirt dresses in stores now

If you’ve been inspired, below you will find some of the most stylish shirt dresses you could add to your closet.

1. White shirt dress 

Crisp, clean and classic, a white shirt dress will go with pretty much everything else in your closet.

Anne Klein corduroy belted shirtdress |

Anne Klein corduroy belted shirtdress

2. Denim shirt dress 

denim shirt dress |

While most of you will have denim in your closet in some form, perhaps because you wear jeans or a denim jacket, how about a denim shirtdress?

Karen (above) wears hers in a simple, stylish way with nude sandals and sunglasses.

Steal her look with this similar denim shirtdress and nude sandals.

1901 chambray shirtdress |

1901 chambray shirtdress

3. Linen shirt dress 

If, like me, you prefer to wear natural fabrics, a linen shirt dress is an ideal travel option.

Also look at this article on stylish travel clothes.

Anne Klein linen shirtdress |

Anne Klein linen shirtdress

4. Long shirt dress 

polka dot shirtdress |

You may usually think about a shirt dress as being a knee-length style, but you could also choose a midi or maxi dress option.

Tanasha (above) chooses polka dots and tie sandals.

Check out this similar polka dot shirtdress and lace-up sandals.

Topshop paisley print shirtdress |

Topshop paisley print shirtdress

5. Satin shirt dress 

For a luxe look, opt for a fabric such as satin or silk, which could easily be worn for a daytime event such as a wedding or for evening.

Forest Lily satin shirtdress |

Forest Lily satin shirtdress

6. Black shirt dress

all black outfits for women over 40 |

There are so many perfect black dress options, and a shirtdress style is one of them.

Deborah (above) chooses an all-black look with red lipstick.

Get her look with this similar shirtdress, pants and booties.

1901 tie waist shirtdress |

1901 tie waist shirtdress

7. Floral shirt dress 

Florals are a popular print for any style or dress. But the print on this H&M dress goes even further by featuring a whole landscape.

H&M silk shirtdress |

H&M silk shirtdress

8. Long sleeve shirt dress 

striped shirtdress |

Many women over the age of 40, or any age for that matter, prefer to cover up their upper arms.

Psyche (above) shows off a stylish long-sleeved shirt dress option.

Get her look with this similar dress below, leather boots, stockings and a Gucci mini bag that she used as a belt bag.

Also look at the best dresses with sleeves.

7 For All Mankind maxi shirtdress |

7 For All Mankind maxi shirtdress

9. Check shirt dress

Plaid is always an on-trend print. A check shirt dress would look good over jeans.

1901 plaid dress |

1901 plaid shirtdress

10. Maxi shirt dress 

a maxi dress and silver booties |

You could choose a floor-skimming maxi like Liv (above). Don’t forget to accessorize with a cute dog!

Recreate her look with the similar shirtdress below, turtleneck top, skinnies, belt and booties.

Ever New maxi dress |

Ever New maxi shirtdress

11. Green shirt dress 

Animal print is a perennial trend. Snake or reptile print has been on-trend for a number of seasons and isn’t going anywhere for spring/summer 2020.

H&M snakeskin-patterned dress |

H&M snakeskin-patterned shirtdress

Below are the shirtdress outfits from above together in a capsule wardrobe. You could easily mix and match the different dresses, bottoms and accessories to create dozens of looks.

A shirtdress capsule wardrobe |

Continue reading:

  1. How To Wear Tunics Or Short Dresses With Pants
  2. The Best Dresses With Sleeves For Women Over 40
  3. The Midi Dress Is Back And We Show You The Best Midi Dresses For Women Over 40

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How to wear a shirtdress: 9 shirt dress outfit ideas for you |

Feature image by Kim


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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