There's a reason jocks are the coolest guys in high schools across the country. They're confident, rebellious, and, more often than not, they grow hair in places the average 17-year-old can't. But above all, jocks are cool because their style is effortless – simple, slightly rugged, a little preppy – and they own one thing everyone else wants: A varsity jacket. Thankfully, you don't have to win a state championship these days to snap on one of the most iconic jackets ever made.

Golden Bear, a San Francisco-based brand that's outfitted kids with letterman's jackets since the 1950s, offers an updated take on this American classic. Its Jackson Jacket, a well-executed mix of vintage nostalgia and contemporary prep, features all the signatures: Leather sleeves, slash pockets, and, of course, the satin lining. "This is the same look we've used since the fifties," says Golden Bear president Schirley Zisman. The one thing that's changed is the fit: It's more tailored than Dad's classic-but-boxy holdover from the Kennedy years, but still leaves ample room for layering. And while varsity jackets are available in limitless color combos, this smart navy and brown mix caught our eyes with its tasteful horn buttons and complementary cuff, collar, and waistband stripes.

Despite its slimmer silhouette, we've found the Jackson to be roomy and breathable, so just layer it over a polo to stay warm this fall. Come the cooler months, add a chunky, cable knit sweater to complete the 'Take Ivy' look. Now's the time, whether you lettered in high school or not, to slip into some jeans, grab those retro-cool shades, and (re)claim your cool. [$495; goldenbearsportswear.com]