The corner of Orchard and Delancey streets in New York's lower east side is dominated by the yellow and black color scheme of an optician's shop advertising complete optical service in 1 hour. Sure, Dr. Harvey Moscot will faithfully fill your prescription like any other purveyor of quality eyewear, but Moscot is otherwise not like any other. Moscot makes and sells some of the finest vintage-style frames in the world. They know from vintage, as an LES institution since four generations back, nearly a century ago, when Sol Moscot first opened his doors on nearby Rivington Street. Moscot's quality and design are, essentially, endorsed by New York City.
A scientific proof regarding glasses, in general: Given that Buddy Holly may have been the coolest man ever to walk the earth, and that Buddy wore some serious acetate frames, then, serious frames are cool. Quod erat demonstratum. Moscot's Originals line is the source for that kind of cool. The Moscot Lemtosh model's extended temple and visible hardware probably match Buddy's signature style the most (the artful John Depp is a noted Lemtosh fan), but the Moscot Nebb's meaty frame would work, too. Moscot also offers a classic aviator shape in the Moscot Zulu. If gold, black, or tortoiseshell tones aren't edgy enough for you, some Moscots are available in other shades of acetate--check out the intellectual Miltzen frame in crystal.
Because their roots are in eyecare, not fashion, Moscot's style doesn't overrule substance. Their sunnies use lenses of real glass, rather than the plastic that fills many designer frames. They use old school tones for the lenses, as well--brown, bottle green, or gray-green, one of which will match your frames, face, and disposition. Of course, you could always go with clear nonprescription lenses. I'm not saying you should wear frames if you don't need to, but men have done far dumber things to look cool.