I wish hats would come back like in the video. Almost everybody wore a hat in 1927. I bought a hat a few weeks back. It's so great to wear, it's safe and warm. However, everybody looks at me as if I am some crazed hipster with my "fedora". If everybody would wear a hat like in the video, life would be so much nicer.
It's really no different than how many people distrust others who wear extremely baggy clothing. Clothing like that has become, rightly or wrongly, associated with gang culture. Most everyday people do not want to deal with others who dress in such a way.
Had fedoras become associated with a more respected culture or group of people today, then they very well could have become more popular.