Gap 1969 Heritage Denim Jacket
Credit: Photograph by Michael Pirrocco

If you're looking for a less expensive and super-classic denim jacket, go with Gap's 1969 Heritage style. It's the style on which more expensive denim jackets are modeled anyway. And, at just under $80 (and even cheaper if you get one of the many used or vintage ones available), you can really wear it out. Roll up the sleeves, get in a fist-fight, crowd-surf: you don't need to worry about it because this thing can take it. Some say it even looks better with years of wear and tear. [$79.95; gap.com]