Summer Fashion 2009

Get your beat-up jeans straight off the rack or ravage a pair yourself. "We used to take drills to ours, shoot BBs at them, or go crazy with patches," says Emily Current of Current/Elliott, the brand largely responsible for the now-ubiquitous boyfriend jeans. Either way, play with contrasts. "I love the look of dressing up our Trash wash with black stilettos and a tiny black blazer," Current says. Cameron Diaz (left) played it perfectly in a pair by 7 for All Mankind.

Far left: Cotton skinny leg with ankle zip, American Eagle Outfitters, $50; at ae.com.