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Roaring Twenties Flapper Fashions for Women

gatsby dresses and hats

by Tina Boomerina (Christina Gregoire)

I don’t know if the current fashion trend started in Hollywood (with The Great Gatsby) or in the fashion industry, but 20’s flapper styles are hot. Of course, you’re probably not going to wear the trend from head to toe, but you can easily update your wardrobe with a few deco accessories, like cloche hats and vintage-style purses.

Or, you can adopt the sleek silhouette and the entire look if you have a boyish figure.

Why the Twenties Roared -  Caution: History Lesson!great gatsby fashion clothing

The Age of Jazz and Craziness must have been a glorious time to be alive.

People who lived through that decade were filled with optimism, freedom, and a sense of reckless abandon. Why? It was a prosperous decade, and a whole lot of fabulous things suddenly became available to the masses:

  • Cars
  • Telephones
  • Radios
  • Motion Pictures

And, people were ready for something new. Romantic, but old-fashioned, Art Nouveau was replaced by sleek, structural Art Deco. And, trendy women threw away their restrictive corsets along with their large, heavy, flowery hats.

gatsby roaring twenties clothes for women over 40 50 60Young, adventurous women fled their small, boring towns in large numbers to seek excitement in the big cities... it was what they had daydreamed about for ages and ages after visiting movie houses to get a dose of non-reality every Saturday afternoon. And, they were able to live their dreams by becoming secretaries in companies that were booming during this period of unprecedented industrial growth. (Goodbye Kansas.)

Photo of Roaring Twenties Fashion

The main photo (above) shows what actual flappers wore. I took an old image and enhanced it so you could actually see the women’s outfits. And, as I was playing in Photoshop, I started wondering who these four women were.

great gatsby clothes and hatsThe original image looks like it is from a newspaper because of the color and resolution (see Resources), so these are neither debutantes nor hookers... the newspaper would not have printed a photo of either group. And, the four women are not chorus girls or fashion models because they are different heights. Read more about designs and colors worn by flappers.

The background in the original image shows a fancy-dancy hotel or speakeasy, so my best guess is that this photo reveals four average, real-life flappers (a bit tipsy), who were leaving a private party (or going to the powder room) when some guy with a camera asked them to strike a pose.

Therefore, you are looking at an image of four Charleston-dancing, cigarette-smoking, fun-loving secretaries, who met at work after fleeing the drudgery of farm life back in Dullsville.

Straight, Boyish Silhouette

You probably already know this, but the standard, rebellious silhouette of the day was long and lean, with a dropped waistline, a high hemline, and a cloche hat (covering a girl's shortly bobbed hair).roaring twenties gatsby

What you may not know is that the flapper style was the beginning of fashion for the masses, because anyone could sew a shift, while earlier couture had to be put together by skilled seamstresses. So, flapper style is “street style.” And, that knowledge may give you a little more courage when deciding what details to incorporate into your everyday wardrobe.

What Real Flappers Wore

I had to figure out what these babes in the photo were wearing when I was “painting” them in Photoshop.

The colors are my own invention and I was just trying to make their outfits obvious, but you might get some ideas by knowing how these women of average means tarted up their looks to fit the trend. (continue to the next page by below or by clicking here)

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Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. theresa

    This article was so fun! I love this era -- I would have fit right in -- in this current era of prohibition I voted yes in Washington State! Our current era also reflects the same type of human expansion and optimism, and yes, rebellion. From the 60s to the current wild, wild web we have opened up to new ways to work, learn and play. We can easily become more of what we want to be - Individual freedoms for personal growth and access to knowledge have never been greater. I truly admire the flappers desire to be free and empowered as women and their designs conveyed these desires. They were brave, fun, definers of a new type of freedom. I especially love many of the shoe designs of that era. Feminine designs with functional heel heights that allow you to be a participant in the fun rather than just being eye candy teetering on 4 inch "sexy" heels. A prime example can be found here: http://www.etsy.com/listing/117171812/1920s-shoes-20s-mary-jane-shoes-walk.

  2. Tina


    Those shoes are smokin'. Love them.

    Cheers, Tina

  3. Amelia

    Fantastic article! I love this era, the elegance and style is hard to find in today's fashion (unless you're willing to pay $$$). Can you please tell me which site or designer/brand the beautiful gold dress on the first page came from? The one with the cocktail style slip underneath and then the transparent beaded material to the floor. I'm hosting a 20's party and I adore that dress. Thanks so much, Amelia

    • Tina-Boomerina


      The gold dress is from Phase Eight in the UK. I hope it's still available. This article was written a while back, but you should check.

      Tina Boomerina

  4. Kelly

    Iam attending a ball which the gold beaded dress would be perfect for theme!! If someone has found it on the phase eight site please let me know!!!