The zoot suit hat first became popular in the 1920s, but by the 1940s, with the US at war, the zoot suit and the gangster culture associated with it, took on a new meaning, raised tensions, and then became an illegal clothes item in Los Angeles County after the Zoot Suit Riots of 1943. Zoot suits have continued to be popular over the decades among latinos, and has often been a suit of choice for weddings and other special occasions. Additionally, the recent revival of swing music and swing dancing has helped increase the popularity of zoot hats in recent years.

Fedoras have a long history of being popular. However, most people - today - associate fedora hats with the swing era, swing dancers, old movies, or as the gangster hat of the 1930s and 40s. The fedora hat is still considered an appropriate part of any man's formal wear, as an accessory to any hep cat's swing clothes, or even as gangster hats for someone's gangster costume.

Cloches: The signature hat of the flapper, the cloche hat was the lady hat that was most popular during the 1920s - the "Jazz Age" - when Charleston was the rage and when the Lindy Hop was born.