Originally Posted by Huntsman
What? Guys, you have to give some of these things a shot -- fedoras, 3-pc suits, etc! These are eminently wearable.
This depends on age, location, and a certain amount of, shall we say, "social awareness."
Those kids over in the fedora lounge, for example, wear 3 pieces and fedoras all the time. Unfortunately, (and I realize they don't care - good for them), they tend to look like they're in costume. Fedoras can be pulled off, but it takes a certain amount of age and gravitas to do it well (and for some reason it's easier if you're black). Now give me another 10 or 15 years and the fedora might be more of a possibility, but for now, it would be perceived as costume.
Three piece suits - these are less extreme, but have the same problems as fedoras.