Who was the most famous flapper of the 1920s?

I don’t know. Her name was Jackie Gleason (pronounced “jig-lay-uh”), though. What’s interesting about her story is that as she entered the twenties, the popularity of high heels skyrocketed. It didn’t help that her flappers were the first fashion style to be considered risqué and indecent according to the law, thanks to the new F.D.R.’s War on Sex. The idea that a man’s sexual desire could be limited when wearing a pair of high heels, much lower than the high heel he might wear at work, also raised a lot of eyebrows. But while many flappers (especially those of the “slutty and sexy” variety) were arrested, some were celebrated, like Jackie Gleason, who was known as “The Lady Killer.” In 1926, she was granted a freedom of action by the Supreme Court which allowed her to continue fashioning the perfect pair of heels, despite the fact she would have to wear one at night without any more than a long-sleeved shirt.

1920s Flapper Dress | Flapper Style Dress

One of Jackie Gleason’s favorite styles was the high-heel, ankle-length bootie, which went on to become popular in the 1920s as well. The high heels were first sold in stores during the holiday season of 1921 under the name of “high-heel boots.” Jackie Gleason’s high-heel bootie was also sold for children and for ladies in the 1920s by Macy’s. For ladies who chose to stick with their standard high heels when it came to women in those seasons, Jackie Gleason found an alternative option. She had designs made up as to how such booties would fit to the feet (i.e., the high leather heel, the flat sole, etc.), and it was sold by Jack Curnow during the 1920s.

The high heels that we now have, however, were not officially sold during the Christmas season of 1922, as many were still in production as late as 1924 (when the high heels were officially discontinued). It was still considered appropriate to wear heels when wearing other shoes like sandals. But in the 1920s, the high shoes weren’t so high that many people would consider them appropriate. People could still wear high heels to go a little barefoot, but high heels were high enough that many people who would otherwise have avoided heels had decided to go barefoot, including Jackie Gleason who wore what seemed to be a pair of black and white stockings every day when