Bloody hell, this is getting like a fashion discussion.
When I go flying I usually wear a pair of jeans or combat trousers and a green NATO jumper... nothing fancy, no badges etc. merely practical stuff.
Wouldn't mind an Alpha CWU-45, would be useful since it can get a bit chilly out on the ramp, but not sure since they're a bit expensive and I wouldn't want to be labelled a "Maverick" wannabe. There again they don't have badges or anything silly on them so they're OK to me.
Not into Ray-Bans or Irvin jackets though... too "Top Gun" for me. Not into that sort of thing.
P.S. Although if you fly a Tiger Moth I do believe that automatically entitles you to wear an Irvin!