Wayfarers were designed in 1952 by Raymond Stegeman. They sunglasses have gone through numerous design modifications during their history. The over sized shades worn by Audrey Hepburn in Breakfast at Tiffany's and the smaller frames worn by Cary Grant in North by Northwest are two examples of early Wayfarer silhouettes. In 2001, the Wayfarer underwent a significant redesign, with the frames made smaller and less angular, and changed from acetate to a lighter injected plastic. The changes were intended to update the frames' style during a period of unpopularity and to make them easier to wear (the frames' previous tilt made them impossible to perch on top of one's head, for instance).The original style of the Wayfarer was re-launched in 2007, and Wayfarers are available in Original Wayfarer, New Wayfarer, and Wayfarer Folding styles as of 2008.

During the 2000s Wayfarer revival, well after the expiration of Stegeman's 1953 design patent,Grey An'ts Grant Krajeckidesigned a larger, cartoonish version of the glasses "so extreme that [they] are best worn by those with a good sense of humor". Sabre Vision's "Poolside" design is a smaller thinner version, that resembles "a cross between old-school Oakleys and the pair worn by Ton Cruiste in 'Risky Business"" designers unaffiliated with Ray-Ban produced several sunglass designs inspired by the original Wayfarers.