I'm like |---| close to getting a bowler. One of those dashes is trying it on. The second is being able to pull it off. The third is the cost. Fedoras are my go-to and my absolute fav, but bowler/derby hats... Yeah, if you wear one and pull it off, it just lends a sense of not only "I don't give a fuck about you and your opinions" but just sheer badassness. XD I mean, come on... Goldfinger's henchman Oddjob uses a bowler hat as a thrown weapon. I think it's even used in several British and American TV shows as a protective device as well. Along with the fedora, the bowler/derby hat is iconic.
EDIT: I also just remembered that bowler/derby hats were actually developed by the British with the original design for horse back riders during fox hunts, I believe. Their top hats kept getting knocked off. So the designer wanted something shorter and rounded to if hit by a branch, it'd decrease the chance of it being knocked off. The original way the bowler was made was like an ultra fancy hard hat too: the customer who wanted the design tested it by stomping on the hat several times. When it didn't break, he bought it.