Grooming & Style

Best Sunglasses to Match Your Face

By Jessica Lothstein

Seems like every summer the sunglass industry (with a little help from Hollywood) honors its favorite decade by reviving a classic from the past. But just because Brad and Leo can get away with Aviators on the red carpet, and the entire male cast of Gossip Girl is partying in reissued Clubmasters like it’s 1959, doesn’t mean you should run out and buy a pair of either -- at least not just yet.

“The rule with sunglasses, just like regular glasses, is that you want to offset the geometry of your face shape,” says Kenny Moscot, co-owner of Manhattan’s famed 90-year-old Sol Moscot Opticians. “If you have a strong jawline or cheekbones, you want to look for glasses with more curves. If you have a round or oval face, you want to look for boxy rectangular frames.”

And unlike trends, your face -- of which there are five basic shapes -- is here to stay. Here’s each kind of mug along with which kind of frames look best.

Round
“Remember this mantra: Round glasses on a round face only make your face appear even rounder,” says Moscot. Instead, look for boxy or rectangular frames to introduce some lines and angularity to your face.

Framous Icons: 1950s Beat Generation, Malcolm X, Johnny Depp 

Try: Ray-Ban’s newly reissued Clubmaster, $140, available at Sunglass Hut (or find a retailer near you at the Ray-Ban Web site); Moscot’s Zelig (Henry Kissinger-esque), $199; Nebb (for Hipsters), $179. The last two are available at Moscot stores.

Square
If you have a prominent jawline, you want to draw attention to the top part of your face (and away from the bottom -- the widest part). “Look for top-heavy frames with some curves to help soften and balance your face,” says Moscot. Square-faced men can’t go wrong with Aviators.

Framous Icons: Fighter pilots (Tom Cruise in Top Gun), G-men (Will Smith in Men In Black)

Try: Ray-Ban’s original Aviator, $130, available at Macy’s (or find a retailer at the Ray-Ban Web site); Tom Ford’s Charles Aviator, $320, available at Nordstrom, Neiman Marcus or Bergdorf Goodman stores.

Oval
You want to visually offset the length of your face, so choose a shape that covers as much of the space between the top and bottom of your nose as possible (known as a deep frame). “And absolutely stay away from small or geometrical frames,” says Moscot. “They’ll make your face look even longer than it is.”

Framous Icons: Run D.M.C. and the ’80s hip-hop scene; the entire cast of “Entourage”

Try: Prada Linea Rossa, $275, available at Neiman Marcus and Saks Fifth Avenue; Polo Ralph Lauren 3039J, $160, available at Sunglass Hut.

Heart-shaped
“Offset a wide forehead and cheekbones with rimless narrow frames,” says Moscot. They’ll draw attention away from the narrowing of your face (downward toward your chin) and prevent the top half of your face from looking bigger.

Framous Icons: Marathoners, police officers, Barack Obama

Try: Ray-Ban 3217, $150; Oakley’s Nanowire 2.0, $300. Both are available at Sunglass Hut and Macy’s.

Pear-shaped
Downplay a strong chin and jaw with semi-rimless or top-heavy frames. “They create an optical illusion by drawing the eye up toward the top of your face and away from the widest part, the bottom,” says Moscot.

Framous Icons: Lance Armstrong (semi-rimless), Buddy Holly (top-heavy)

Try: Oakley Half-Wire 2.0, $175, available at Sunglass Hut or Macy’s; Moscot Lemtosh, $180, Moscot Web site.