I care about the way I look - but according to my wife I look a little bit too put together. I know what she means but I'm unsure how to wear my clothes with more "disrespect." I have a friend who wears the same stuff - MTM Italian suits etc and he treats his things like crap - tosses them in a heap on a chair all day long etc but when he wears them they look much more a part of him. He has the most creased linen jacket I've ever seen yet it looks great on. I, though, look like someone has taken a lot of trouble dressing me perfectly to the last detail. Do you worry about this? Are there ways you dress as if you don't really care what you've got on? I'd rather look a little more "couldn't care less."