We Love This Iconic One-And-Done Fashion Staple That Never Fails To Impress

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The first time I gazed upon a shirtdress, I was in middle school and at my cousin’s wedding in Manhattan. 

There was a woman wearing what looked like a white collared Oxford shirt — but it was also a dress. 

It had a structured top, a drop waist, and ended in three paneled ruffled pieces. She paired it with a suede brown belt and matching high-heeled slouch boots. 

I asked my mom for that outfit. She said, “Molly, those are Gucci boots. You’re 10 years old.”

“I know I can’t have those. But what about the shirtdress?” I bargained. 

She said, “We’ll see.”

Which was her way of saying “probably not.”

But my mom came through — she had a white Donna Karan shirtdress that she rarely wore. It wasn’t the same, as it was straight and looked more like a really long Oxford, it was close. 

And so began my obsession with buying every shirtdress I could find. 

Shirtdresses for women were originally called “shirtwaist dresses” — they came about in the 1950s.

At Christian Dior’s post–World War II “New Look” couture designs, the designer debuted a more feminine version of a long men’s shirt, which turned into the iconic trend that remains a fashion favorite. 

The best thing about a shirtdress is you can wear it alone or layer it — throw on a cardigan or chunky wool sweater on top, or wear a turtleneck under it in the chillier months. 

Wear it with wool tights and boots, cute platform loafers or chunky sneakers — the possibilities are endless. 

We made a list of our fave must-haves below!


This little English Factory darling is on its way to my house as I write this. The shirtdress has a unique layered effect, thanks to the combination of a knit bodice and contrasting poplin skirt.

SHOP – $90

The ASOS Design organic cotton mini shirtdress in white features a spread collar, button placket, and a curved hem. Perfect for a Saturday out and can be worn alone for a casual look or accessorized with a belt or a chunky cardigan.

SHOP – $29

Another ASOS Design cutie is the cotton mini smock shirtdress that comes in black, white, and khaki. The relaxed fit makes it a perfect fall outfit that translates from weekend errands to a night out. 

SHOP – $32

This nap oversized boyfriend shirtdress is casual, baggy, and tons of chic! It features long sleeves, one pocket, a fold-over collar and covered buttons. This classic signature is a must-have and comes in butter cream and gray.

SHOP – $68

Free People’s Penny Shirtdress in rainbow combo is the very definition of casual boho chic. It features a free and flowy, button-front silhouette with floral embroidery throughout for added dimension, ruffled sleeve cuffs, and pleating at bottom. 

SHOP – $108

The Gap’s flannel plaid shirtdress is always a solid buy. With a straight silhouette and relaxed fit, it hangs mid-thigh and can be worn lounging around the house or about the town. 

SHOP – $79.95

The ELOQUII Button Down Maxi Shirtdress comes in hunter green, a polka dot or zig zag pattern. It’s an elegant, flowy take on the shirtdress.

SHOP – $129.95


Do you love the shirtdress and the modern takes on the classic look as much as we do? Let us know below! 

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