Fedora

Fedoras were first worn in the late 1800’s and was popularized in the prohibition era of the 1920’s, and is often associated with gangsters of that era such as Al Capone and Machine Gun Kelly. While popularized by mobsters in the roaring 20’s the fedora is still popular now, often worn at formal events such as weddings and dinner parties. The ability to be worn by gangsters on the streets of Brooklyn and dads at Kentucky derby parties speaks to the Fedora’s flexibility and style.  Depending on who is wearing the fedora, it can also be one of the most intimidating hats on the list. Two examples are the legendary football coaches Paul ‘Bear’ Bryant of the University of Alabama, and Tom Landry of the National Football League’s Dallas Cowboys franchise. Placing a hat with such style on an extremely masculine figure creates an imposing presence. While it is very stylish the Fedora isn’t as comfortable as some of the other hats on this list, and there also isn’t much use for it during especially cold weather. Despite that, the Fedora is an embodiment of class, and a great hat overall.