I think one of the bigger shames of the modern era is that gentlemen’s hats are not fashionable anymore. Every movie from the 1920s to probably the 1950s featured men in stylish fedoras and trench coats, but nowadays those things are decidedly either pretentious or creepy (and most probably both). I think Justin Timberlake can pull a fedora off, for what it’s worth.
Now I’m not really one to talk much about fashion anymore. When I played in a band I liked to play around with wearing different styles and colors just to shock or interest people, but I feel a bit out of touch with all that nowadays, and actually I’ve pretty much reverted to just being a “dude” again when it comes to fashion.
That having been said, I still feel like I need a good hat, especially now that I’m kind of in-between having a regular haircut and long hair. A good hat would hide the in-between, incredibly awkward stage. That’s why I got online and found this article about matching a good hat to your facial shape.
So I would say that my facial shape is pretty much squarish. As a result, the article recommends two possible hats for me: a Homburg or a Bowler. Actually I think these are kind of funny/cool hats, and probably not as pretentious as fedoras. But still a little pretentious.
Now I just have to figure out how to make these hats less pretentious. Perhaps if I could convince about 10% of the U.S. population to wear one, it would be more socially acceptable?
Pop Quiz: What is the least pretentious hat in world history? Answer. Which is ironic, because in its hey-day the purpose of that hat was to be as pretentious as possible.