A man adopts the urban-water-skier look for one of two reasons. The first is obliviousness: The wearer is the kind of guy who simply hasn't purged himself of collegiate artifacts like futons. The second is intent: The Croakie-adorned man aims to telecast athletic prowess, to suggest that while he may sit behind a desk 40 hours a week, he's fully capable of riding waves like Kelly Slater, bra'. Neither of these explanations makes it okay for a man to look like Matthew McConaughey from the neck up and Lee Iacocca from the neck down.

"Wearing athletic sunglasses with work clothes doesn't make a good impression," Larry Leight, cofounder of Oliver Peoples, says. "It looks like you don't care whether or not you get ahead." Ironically, high-octane sunglasses secured with neoprene straps are most often worn by men who are trying to get ahead.

"You see them at airports a lot," says Marcus Wainwright, cofounder of the label Rag & Bone. "They're usually on guys who are wearing very large pleated trousers with a BlackBerry clipped to the waist."

The guys Wainwright refers to might argue that hanging athletic goggles around their necks is practical, a necessary evil—just like their PDA holsters. But is the risk that their eyewear will fly off—that a rogue volleyball in need of a spike crossing their path on their way home from work, perhaps—really all that high?

Leight offers an analogy for anyone still struggling to grasp the difference between wearing a sport-inspired accessory and yoking yourself with sunglasses that are clearly as essential to your daily activities as a scuba mask: "You can wear a suit with tennis shoes, and that can look good," he says. "But you can't wear track shoes—the kind of sneakers designed for performance—with a suit."

Well, you could. But the thought of pairing Nike Air Maxes with a custom suit should be enough to dissuade you from experimenting. The same logic applies to strapping on a pair of Oakleys for an average workday. No one's saying you have to put on J. Lo—glamorous sunglasses because you're wearing a Black Label suit, but you might want to bypass the "I just got off a Jet Ski" breed for something more subtle. If you're striving to show you have a sense of style, Iridium lenses aren't going to get you there.

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