This Vintage Style Staple Flatters Every Shape—How To Bring The Shirt Dress Into 2024

As someone who’s passionate about vintage style and has always loved fashion history, there’s one clothing item that, to me, personally defines our transition into “modern” women’s fashion. I’m fascinated with the style of the 1940s, and the ‘40s (on into the ‘50s) were all about the shirt dress.

The ‘40s represented a time when women’s fashion was under pressure to become more practical as women joined the wartime workforce but also had to maintain social standards for femininity and elegance. Hence, we got the shirt dress, which had existed before, but was perfected in the 1940s as that iconic combo of military-inspired style that still flattered the feminine shape.

The one-piece garment featured a button-up top inspired by menswear (often with a lapel-style collar) and a midi-length skirt, usually set off by a belt. Shirt dresses were easy to wear, easy to take care of, and kept women looking chic. Unlike the styles of the past, they also didn’t take a lot of fabric to make, a necessity during wartime rationing. 

In my opinion, they really set the tone and created the moment for women’s fashion today – clothes that emphasize our femininity but suit our active lives. Best of all, they’re universal, can be dressed up or down, and look good on every body type. 

We still see shirt dresses produced in 2024, but as a vintage style staple, I think they’re sometimes overlooked. They’re one of the easiest, most comfortable, and polished ways to add timeless style to your closet.

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Why Do Shirt Dresses Look Good on Everyone?

Here’s what I love about this item: Shirt dresses create a sense of structure on the body without being tight, uncomfortable, or overly formal. They also provide a great balance between the shoulder and the A-line skirt, which works really well visually on most women. 

Shirt dresses create the sense of a balanced figure and smooth out imbalances between top and bottom. For instance:

• If you have strong shoulders, the A-line skirt balances them out. 

• If you have smaller shoulders, the cut of the top and sleeves makes them look larger. 

• If you have a larger chest, the overall balance smooths and de-emphasizes this. 

• If you have a pear shape, the dress highlights your torso while gliding over larger hips.

The basic shape of the shirt dress creates an elegant hourglass. And the line of buttons in the center creates this beautiful sense of symmetry. 

Some Vintage (and Royal) Style Inspo

The shirt dress has experienced a renewal of interest since TV shows like Mad Men and The Marvelous Mrs. Maisel aired. Here are a few of my favorite shirt dress style moments from those shows:

And any discussion of the shirt dress wouldn’t be complete without mentioning Princess Kate, who has made the item one of her style staples as an icon of modern elegance:

How To Bring the Shirt Dress into 2024

Of course, we’re no longer in the ‘40s and ‘50s, and most of us aren’t attending royal engagements. So how do we keep the core of this style while updating for today?

The great thing about the shirt dress is there are ways to lean into its vintage history or more modern silhouettes. Check out some modern takes on this classic style below:

If your shirt dress doesn’t come with a belt, you can always add one. Or swap out the one it comes with for a different look. Try traditional leather or a brighter color for added contrast.

Summer shirt dresses can be repurposed for fall. Add a heavier cardigan or jacket, tights, and boots. 

Maxi shirt dresses that button all the way down can be partially unbuttoned for a trendy take on the look. 

These dresses are great options for vintage-inspired style or 2024 updates:

Rihoas The Black V Neck Button Puff Sleeve Midi Dress, $45

Rihoas The Blue Lapel Tunic Sleeveless Midi Dress, $52

Boden Libby Jersey Midi Shirt Dress, $130 

Lulus Central Park Sweetie White Linen Collared Button-Up Mini Dress, $25

Tuckernuck Chambray Callahan Shirt Dress, $128 

J.Crew Elena Shirtdress in Cotton Poplin, $168

Lulus Italian Summer Beige Linen Midi Dress, $69

How To Thrift the Shirt Dress

If, like me, you're interested in sustainable (affordable!) fashion and vintage styling, there’s one thrifting hack I love to share when it comes to shirt dresses. I’ve actually built much of my own wardrobe on this foundation by knowing what to look for. 

The 1980s experienced a revival of ‘40s and ‘50s fashion which is sometimes known as “‘80s does ‘40s.” Designers produced a ton of pieces that looked similar to ‘40s dresses, but were more modern in sizing and “wash and wear” by our standards. ‘80s does ‘40s dresses are still fairly easy to find in thrift stores and on resale apps today, and they give you the look without the fragility and worry of owning a midcentury vintage piece. I look for ones that have a timeless vibe, and I often update them by removing any shoulder pads. 

I own both polished “work-appropriate” shirt dresses and really relaxed versions that still allow me to feel put together when I go to the grocery store. They’re basic and comfortable, but get me compliments without fail.