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.
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.
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.
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.
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.
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.
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.
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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