Ok, I probably know the answer to that question, because you look ridiculous, but think of the benefits of this hat!
First off, when someone makes fun of how ridiculous you look you have your hands free to shoot them (not recommended.)
Also, you won't have to do that stupid move when you are trying to carry stuff, where you put the umbrella between your neck and shoulder and try to balance it. The result of this move will always be the same: You drop both the umbrella and everything you are carrying.
Again, I understand it is not the most fashionable item ever created, but neither were Crocs and that didn't stop them from being popular. We are too obsessed with how we look in this day and age, and have put too much value in our looks. Ladies, what's sexier than a confident man who doesn't care about what others think of how he looks, as he confidently walks down the street with an umbrella attached to his head??? (Answer: Just about anything)
I say let's start wearing them! You go first . . .