Small and Round: John Lennon, Samuel Beckett, David Foster Wallace
These nerdy glasses, popularized so much by Lennon that no drugstore ’60s hippie Halloween costume would be caught dead without them, actually point to bigger and better things. Lennon, Beckett and Wallace are all heroes of experimentation, pioneers, each trying to push the limits of their craft. All three are rebellious and witty, though at least two out of three are impenetrably bleak at times. If you wear these glasses, you may be a dashing rebel revered by your peers, but watch out: they’re going to expect some genius out of you.
Old Man Glasses: Donald Barthelme, Ernest Hemingway, William S. Burroughs
It seems as though old man glasses are exclusively worn by writers (and girls in Brooklyn trying to be writers), so if you wear these, be prepared to produce. You should be so busy, in fact, that you can only buy your spectacles from the drugstore, which may account for the spindly frames. These three are very different writers, however, so pick your poison — Barthleme is playful, a pioneer of postmodernism, Hemingway is sparse and understated (and arguably misogynistic), and Burroughs is a wild, experimental, drug-addled Beat writer. But all of them write wonderful prose that have shaped and will continue to shape our literature and culture, so you really can’t choose wrong. If you wear these glasses, you might become addicted to something, but hopefully you’ll at least get a novel out of it.
Square Frames: Jonathan Franzen, Allen Ginsberg, Johnny Depp
Ah, the ubiquitous “hipster” glasses, sold at Urban Outfitters everywhere. Well, there’s a reason for it. Who wouldn’t want to emulate this set of fine gentlemen? Don’t forget that in October, someone stole Franzen’s specs and demanded a ransom of $100,000 (he was “just bored”). These glasses seem to fit everyone — the semi-loathed but undeniably talented “Last Great American Novelist,” the boundary-shattering Buddhist Beat poet, and the paradoxically reclusive actor and heartthrob, who was in Edward Scissorhands, but also The Tourist. So, if you wear these glasses, you’ll either fade into the crowd or, like these fellows, stand out on your own accord, no face-adornment needed.
Cat-Eye: Marilyn Monroe, Katy Perry, Agatha Christie
Lest you think only your weird Aunt Mildred has ever rocked the cat-eye, here are three women who did it almost as well as she. From Agatha Christie, the best selling author of all time (which — wow! Point for the ladies) to Marilyn Monroe, actress and adored pop icon, to Katy Perry, who, no matter what else you might say about her, does it her own way all the time. Thus, the cat-eye appears to be a symbol of strength and confidence, and maybe a little of feminine wiles and grrl-power. If you can pull of these babies, you’re probably confident in your own skin and ready to kick ass. Just don’t play dumb for too long.