18 Shirtdresses to Wear Every Season

There are pieces we buy that we’re head over heels in love with, then they sit untouched in our closets because we don’t have the right occasion to wear them to. They’re only truly fabulous when they’re being worn — and we’re getting our money’s worth. But that’s not the case with shirtdresses. The stylish staples will remain in rotation in your wardrobe because they work for a myriad of events and across all seasons. A shirtdress is a polished choice for when you’re working from home, especially if you need to jump on a Zoom call. Plus, shirtdresses can be worn to brunch or running errands. In other words, all week long. Add in some statement earrings and a pair of heels and your favorite shirtdress can be carried into evening. Unlike flip flops and straw hats, the right shirtdress can transcend seasons and help you master confusing trans-seasonal dressing. When the temperature goes down, swap sandals for boots. You can even work in a pair of tights or slip jeans on under the dress. To fully understand just how versatile shirtdresses are, you need to own one. Keep reading to shop shirtdresses that will see you from the end of summer into fall and beyond.

Shirtdresses 2021 Update

Shirtdresses 2021 Update #1

Mango Cotton Shirt Dress, $49.99 at Mango
Shirtdresses 2021 Update #2

Nanushka Rowan Poplin Shirt Dress in Creme, $575 at Nanushka
Shirtdresses 2021 Update #3

COS A-Line Shirt Dress in Bright Green, $115 at COS
Shirtdresses 2021 Update #4

Dries Van Noten Printed Cotton Poplin Shirt Dress, $514 at mytheresa.com
Shirtdresses 2021 Update #5

& Other Stories Collared Twist Detail Midi Dress, $119 at & Other Stories
Shirtdresses 2021 Update #6

Le Sirenuse, Positano Lucy Wind-Print Cotton Midi Shirt Dress, $438 at Matches Fashion
Shirtdresses 2021 Update #7

Eloquii Maxi Full Shirtdress, $69.99 at Eloquii
Shirtdresses 2021 Update #8

R13 Boxy Button Up Dress in White, $450 at R13
Shirtdresses 2021 Update #9

Zara Printed Shirt Dress, $69.90 at Zara
Shirtdresses 2021 Update #10

Tory Burch Printed Shirt Dress, $413 at mytheresa.com
Shirtdresses 2021 Update #11

COS Wrap Shirt Dress, $115 at COS
Shirtdresses 2021 Update #12

Free People Little Daisy Shirtdress in Sunshine Combo, $148 at Free People
Shirtdresses 2021 Update #13

Nanushka Noor Cut-Out Slip Satin Dress in Desert Rose, $388 at Nanushka
Shirtdresses 2021 Update #14

Mango Cotton Shirt Dress in Beige, $79.99 at Mango
Shirtdresses 2021 Update #15

Lemaire Twisted Cotton Poplin Midi Shirt Dress, $650 at Luisa Via Roma
Shirtdresses 2021 Update #16

Gimaguas Pia Dress in White & Red, $150 at Lisa Says Gah
Shirtdresses 2021 Update #17

Acne Studios Satin Shirt Dress, $348 at mytheresa.com
Shirtdresses 2021 Update #18

Universal Standard Peyton Poplin Shirt Dress in Royal Blue, $77 at Universal Standard