-By Michael Macko, Details Fashion Director

Photos by Michael Macko

During a recent weekend in the city, I went shopping to escape the heat, and I realized that everything I bought—and nearly everything being sold—was either vintage or made to look that way.

I love items that have an instant history—that have already been worn in, broken in, and distressed. The Japanese have a philosophy called wabi-sabi, which essentially says that nothing is perfect and that the beauty is in the imperfections. So when the T-shirt you just bought already has holes in it, you don't worry so much about spilling your macchiato on it. Go ahead and drip. Sure, the threadbare, tattered look isn't entirely new (hello, Abercrombie), but the guy who's wearing it is.

My friend Seth Weisser, co-owner of the vintage clothing store What Comes Around Goes Around and the designer of the nostalgic collection of the same name, has his own theory about perfection. As he puts it, "Most men have to be polished and dressed up all day long, so when they relax they want to be in a comfort zone." He also cited what he calls vintage frustration as one reason for the success of his own line and lines like Nike Vintage: The perfect, well-worn items that would take weeks or months to find scouring flea markets or trolling eBay are now readily available to you pre-distressed—and in your size.

Alex Carleton, the founder and designer of must-wear label, Rogues Gallery says, "The worn-in hand of a great vintage T-shirt—when the cotton has the perfect texture—is such an amazing find. I am interested in the patina that things develop with age—and how that effects that garment and connects you with a different time and place." And you thought you were just wearing an old shirt.

Info on where I bought my favorite new, old, and old-looking finds is below.

Re-worked vintage "Atlantic" T-shirt ($95) by Rogues Gallery available at roguesgallery.com.

J. Crew vintage-style ID bracelet ($150) available at jcrew.com.