Ray-Ban® Clubmaster® Fleck Sunglassesfrom Madewell$160
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Before reaching iconic shades-makers status, Ray-Ban got its start making glare-free lenses for Air Force pilots in the '30s. The perfect mix of old school and new school, these are the kinds of sunglasses that are so timeless, they'll never need to make a comeback. Case in point: these retro-inspired specs in tortoise with metal accents. Acetate. Import. Madewell. com only.