Ya know what they say, "The Suit makes the man!"
start with the ugliest plaid suit you can find. butterfly collar, huge bow tie etc etc. and ya wear that suit and ya wear it with pride.
Peeps is gonna take notice, no doubt about that! Ya gotta have fun doing it, or your just gonna come off looking dorky. However, if its all in good fun and your willing to laugh at yourself, i'm sure others will join into the fun themselves. Be sure to flip your hat, and a walking stick is always a riot. Just think chapman (charlie)
from there ya just gotta incorparate fun retro games into your program, ride a vintage bike to school, bring in your old board games, heck have somebody drop you off in an old rat rod. do something new every week. It's all gonna be 1000x cooler than the ugly plaid suit.
Once people start asking "whats coach j upto this week", the battle will be won.
Besides it's all american history. The more ya get to join in your fun,
the bigger the "up yours" when your stickin it to the man!
edit* guess my point is, it starts with you. have fun, enjoy the things you enjoy and its sure to be contagious. Even the neigh sayers will join in, if it looks like fun.