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Roaring Twenties Flapper Fashions for Women

gatsby dresses and hats


What Real Flappers Wore (continued)

...Refer to the main photo above.

1. The tall, skinny flapper in green is wearing a sleeveless top (untucked) over a pleated skirt. It looks like she either sewed or tied striped fabric over her cloche and tied a long, striped scarf, of the same fabric, around her neck. You could get the same effect as the hat by tying a geometric-patterned scarf around your head.

history of flapper fashion2. The flapper chick in pink is wearing a sheath over a camisole. It looks like she belted her dress around the hips with a sash and pinned a huge polka-dotted bow to the neckline. I may have drawn her hemline wrong… it was difficult to tell. (And, I’m sorry if she’s your great-great-great granny, but she looks like she has been overindulging in the hooch… lol.)

3. The petite flapper in yellow appears to be wearing a sweater with a band at the bottom (or a sash around it) over a pleated skirt. She has a very long scarf around her neck, held in place with a clip or a buckle.

4. The flapper in blue has a bit more cash because her outfit is terribly chic. She is wearing a dress (or a two-piece dress) with panels of fabric that flare out, exposing an under-skirt. Her necklace looks like fringe that flies around when she dances.  And, her hat (which probably matches the dress) looks like it’s embellished with a pleated fan of the same fabric.

Two of the girls are wearing Maryjane shoes with thick, medium-height heels. You can find something similar by looking at dance shoes… ‘cause these babes are dressed for frantic dancing.

Flappers Were Rebels

gatsby dress for occasion eveningsYes… we can only imagine how horrified the mothers of these girls must have been when they saw this photo. Just a generation prior, it was shocking to see more than a woman’s ankle, but when these babes kick up their heels, you can see the tops of their stockings as well as their longer-legged knickers. Pass the smelling salts.

Flapper Accessories

If you aren’t skinny or flat chested, you can still wear 1920’s accessories with your T-shirts and jeans or your midi-length dresses. Look for these flapper accessories:

  • Shoes: Round-toed Maryjanes and T-straps.
  • Hats: Newsboys and cloches. (Larger brimmed hats, with simple styling, were also worn.)
  • Jewelry: Art Deco bracelets, pins, and cuffs. Layers of beaded necklaces.
  • Handbags: Beaded purses and bags with deco-style metal details.
  • Makeup: Kohl-rimmed eyes, red Clara-Bow lips.

Don’t wear these things if you don’t love them, but if you have always had a defiant, rebellious streak, Roaring Twenties flappers (and their accoutrements) are ongoing symbols of liberated women throwing off the restraints of outdated Victorian repression. And… the hats are cute.

More Articles for Baby Boomer Women:

Cloche Hats for Women With Short Hair

What to Wear for Cruise Dinners and Formal Nights

Types of Hats for Women & When to Wear Them: Fedora, Cloche, Victorian

Shopping Tips for Chic Baby Boomer Women


Roaring Twenties Fashion for Women

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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!!!