A good pair of sunglasses is arguably more defining than an entire wardrobe. Think Tom Cruise in Risky Business—nothing against his yuppie attire, but it was his shades (and that Porsche 928) that imprinted the nonchalant cockiness and charismatic appeal that shot the relatively unknown 21-year-old actor to stardom. In case the ’80s classic is a blind spot, Cruise wore Ray-Ban Wayfarers.
There’s something about these particular specs—the timelessness, the sense of effortless cool, the hint of rebellion—that has given them a longevity few eyewear options can rival. (Realistically, only the aviator can compete.) From JFK, lounging in khakis and an Oxford on Martha’s Vineyard, to John Belushi in The Blues Brothers, Quentin Tarantino’s entire crew in Reservoir Dogs, Andy Warhol and Bob Dylan in their prime, to the ultimate—Muhammad Ali—these rectangular shades aren’t just classics. They’ve reached icon status.
Ray-Ban first introduced the style in 1956, and the draw was near immediate. Since then, the Wayfarer silhouette has become a key style across brands. Why do they hold such lasting appeal? Perhaps it’s their democratic structure—the rectangle frame fits all face shapes, though Wayfarers look particularly good on round and oval faces. If you have a low bridge (the bridge of your nose sits level with or below the pupils), these will suit you even more. But, they’re arguably more about attitude. A well-designed wayfarer combines traditional masculine polish with a confident energy that’s hard to miss. The trick to picking the ideal pair? We’ve done the leg work for you with our definitive guide to Wayfarers, below.