Over the past five years, Venice Beach–based Lipsky, 41, has shot more than 30 stories for Outside, including March's cover image of Jack Johnson. But the former Telluride, Colorado, fly-fishing guide had no interest in being shot by a colleague—until we told him the colleague was Chris McPherson. "Chris and I assisted [celebrity photographer] Mark Seliger together way back when," says Lipsky, "so it was really fun to hang out with him again." It also helped that Lipsky was able to pick the set, a friend's backyard down the street from his studio, complete with a bocce court, hammocks, takeout barbecue, and McPherson's French bulldog, Steve. "Our dogs were getting in and out of the shots all day," Lipsky says.

On Lipsky: Boulder Plaid Western Shirt ($68) by Lucky Brand Jeans; Basic Crew ($17) by Banana Republic; 514 Slim Straight Jeans ($44) by Levi's; Classic Slip-ons ($40) by Vans; Oyster Perpetual Submariner Date watch ($5,850) by Rolex.