The history: Flashback to the 1930s, when the Aviator emerged as the standard-issue frames for the military, and Ray-Ban became the first sunglasses brand in the world. The anti-glare specs were made popular with men like General Douglas A. MacArthur and decorated pilot John A. Macready, who set flight records in the early ages of aviation.
Back then, most pilots wore goggles, so Ray-Ban developed the "anti-glare" Aviator. The lenses' iconic teardrop design fit around pilots' oxygen masks, making for a practical (and, nowadays, effortlessly stylish) look.
Style points: "The aviator frame also looks good on most people, but it works best on a heart-shaped face, drawing attention to prominent facial features," DiPalma says. "The thin metal frames with broader bottom halves highlight proportion throughout the face, and widen the appearance of the chin." The classic silhouette and opaque, glare-free lens is best-suited for guys with a military-inspired style.