I find it really awkward when former rocker/"cool celebrities" get into their 50's and older and they try to cling to some kind of hybrid old/new hip style that really doesn't look good at all. 1 - She is a fashion model, the idea that she doesn't know what fashion looks good on her is true irony. 2 - He is the "King of All Media", a supposed alpha male and he is letting this chick pick out all his clothes. 3 - He hired a guy (Ralph) and that hair lady (forgot the name) and their only job in the whole world is to make this guy look good and they have failed at it in spectacular fashion for 2 decades. Again, true irony. His fashion actually got really really bad 15 years ago when rock music died out. He started wearing fluffy open pirate shirts (like that Seinfeld episode), weird vests, unflattering tank tops, leather pants, etc. ----------- Their fashion is bad but the hat thing just irks me. It's like when children find a closet full of old clothes at grandma's house and try everything on. Or like the children's interpretation of a Hollywood costume department, they find a mish mash of random costumes from different eras and just try wearing them all.