Chuck It

Converse Chuck Taylor's are the most successful selling basketball shoe in history (according to Wikipedia). There is no reason why they should be chucked (pardon the pun) with your varsity jacket* when you leave high school.

When paired with fitted jeans rolled up for that old-school feel or a pair of khakis, you can be Peter Pan and never grow up.

Avoid graphic tees displaying your favorite band or a naked girl plastered on the front. Keep the top mature/casual with a cardigan, sweater or plaid shirt. Extra sophistication-points for throwing on a blazer.

*I'm aware that varsity jackets are "in" this season. (In my honest opinion, they really shouldn't be. Grown men should not be dusting off old football/track jackets in hopes of reliving their glory days. Keep it in the very back corner of your closet and only bring it out when:

1. You are showing your son that you were once a great athlete or 
2. Your girlfriend wants to role-play the whole teacher or cheerleader and football player fantasy...)