When I start up a game, I'm usually in my pyjamas (sleep, wake up, game, eat, game, sleep. Wash, rinse, repeat). 24/7 (excepting when I need to shower and put on my ALTERNATE pair of jet-black pyjamas.)
When I'm in my groove, I have a black fedora. I'm in pinstriped night clothes and I still make it look awesome.
Even better? I can fit it over my Xbox360 headset.