The Flapper

Two flappers dancing *on the edge of a roof. In heels.*

The quintessential Twenties (American, Western European or sophisticated) woman. A young lady ever more spirited than the Spirited Young Lady, thanks to feminine liberty. She danced the Shimmy and the Charleston, wore make-up for the first time since the 18th century, drank with the boys, and enjoyed various other delights The Roaring Twenties had to offer. Short hair, short skirts, short, loose & low-waisted evening gowns, high rolled stockings, boyish figures, and swanky cloche hats were a must.

Their sexual liberty was a result of women's growing hatred of the classic Double Standard; that promiscuous men were "studs," while promiscuous women were "whores." In their eyes, men and women were equal, so they could be just as sexually free. Another factor was the then popular view of women as house wives and mothers who should be subordinate to their men and preferably not leave the house.

Examples of The Flapper include:

Anime and Manga

Gina in Porco Rosso, as befits the early depression setting. Especially apparent in comparison to the Edwardian dress she wears in her flashback.
In the "epilogue" episodes of Steel Angel Kurumi, Saki embraces the flapper aesthetic - not the overtly sexual version popularized by Clara Bow, but the earlier, more innocent type popularized by Colleen Moore.

Film

Evie in High Road To China.
Almost all the women in The Cat's Meow. As a bonus all the costumes are black, white, and gray so they look like Edward Gorey characters.
Peppy Miller in The Artist.
- Every woman in The Artist.
Most of the women in Singin' in the Rain, with the notable exception of Lina.

Literature

The Great Gatsby: Most of the females in the novel.
The Sun Also Rises: Brett.
In another F. Scott Fitzgerald novel, Gloria in The Beautiful And Damned. Since the novel is set in the 1910s, she is explicitly said to be an early proponent of the fashion.

Theater

Chicago.
No No Nanette originally had the Opening Chorus "Flappers Are We."
Most, if not all, musicals set in the 1920s or 1930s in a major American city.
- Anything Goes
- Thoroughly Modern Millie
- Singin' in the Rain
- The Drowsy Chaperone does a nice job of satirizing this trope.

Web Comics

Dinosaur Comics: T-Rex is very interested in flappers.
Ivy in Lackadaisy, to the point where Rocky warns her not to come and see his conservative Catholic aunt.

Web Original

The "old-timey" Homestar Runner video "It's the Sneak!" mentions flappers and features Marzipan dressed as one.

Western Animation

Betty Boop: None other than the Boop herself.
In The Simpsons, we once see a photo of Marge's mother in her flapper days.
This was the original characterization for Minnie Mouse, however times faded and she lost her flapper look.

Real Life

When Joan Crawford came to Hollywood in 1925 she promoted herself by entering and winning dance contests doing the Charleston and other routines of that era. Her early roles often featured her dancing skills.
Clara Bow, the original IT girl, was Hollywood's foremost flapper in the 20's.
Louise Brookes and her iconic bobbed hair.