Vintage Feminine for Valentine’s Day

In spite of the huge trend in the 1920s for women to sport a more tomboy look (short hair, shapeless dresses, and sportswear inspired by men’s fashion), it can never be said that women back then looked anything other than feminine.

The outfit below was modeled in 1919, a year before the decade of my current fascination, but it helped to inspire the feminine look I created for a night on the town with Hubby celebrating Valentine’s Day.

Photo of a model in a dress from 1919 from page 241 in the book "Fashion: The Definitive History of Costume and Style"
Photo from page 241 in the book “Fashion: The Definitive History of Costume and Style”

Notice the draping fabric and the oversized pockets in the illustration, then take a look at my own creation below. You may recognize this look from a previous post when I was working out the details.


The silk shirt dress from Eileen Fisher is a modern spin on the dress in the illustration above. They both have big pockets around the hips and buttons down the front. My dress, though, opens up to become a lightweight, unstructured jacket over the slip dress beneath. It reminds me of the style modeled on the far right in the illustration below.

One of the benefits of this outfit for petites is the elongating line created by the color of the slip dress. That line, along with the movement of the fabric, also does a nice job to camouflage my midlife middle. In addition, my upper arms are covered and, as I get older, this has become more important.

1920s-inspired Valentine's Day outfit -- an unstructured gray Eileen Fisher shirt dress unbuttoned to reveal an ivory slip dress beneath. Paired with gray tights and beige, high heel Christian Louboutin mary janes.

I have to admit, one of the things I’ve learned from trying on this version of the Twenties is that I’m not as fond of the unstructured look. It can border on sloppy if I’m not careful — and sloppy is not how I like to dress for Valentine’s Day. But I like to think the fabrics I’m wearing, along with the (fake) pearls and high heel mary janes help steer everything toward a modern vintage chic. Let’s hope the hubby agrees.

Happy Valentine’s Day, everybody! And, to all my gal pals — Happy Galentine’s Day!


Shop this look:

Eileen Fisher Silk Shirt Dress: Similar here and here   |  Eileen Fisher Silk Slip Dress: Similar here and here   |  Eileen Fisher Gray Tights  |  Christian Louboutin Mary Jane Heels: Similar here and here  |  Vintage Long Strand Necklace: Similar here and here


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    • Thank you, Jodie! It was fun to try this outfit. It’s one I’ve been thinking about for a while. I really love the fabrics more than anything else. I owe you an email, by the way! I’ve started, but have been pulled away from my computer off and on today. Look for a good response tomorrow! 😀 And thank you for checking out my post!