In fact, it's not uncommon for the messiest guy in the office to also be the most heralded, a phenomenon that has made its way into popular culture. In Dana Vachon's recent novel, Mergers & Acquisitions, the only clear hero is the poor overweight slob to whom all J.S. Spenser's dirty work has been outsourced. The other guys—the ones who can tell the difference between a Turnbull & Asser and a Thomas Pink shirt "blindfolded"—are not so laudable.

Women can take even more criticism if they seem overly concerned with their dress—often at the hands of female superiors. "I'm more 'fashiony,' which is definitely misunderstood and under-appreciated in my line of work," wrote a V.P. at one of New York's better banks. Sport more tailored and modern clothing and you get hit with a double-whammy—not only are you not working hard enough, you're trying to distract everyone else from their business.

If you think that's all hooey, I'd ask you to recall the time Hillary Clinton showed up on the Senate floor revealing a centimeter of cleavage under her rose-colored blazer. No one went so far as to accuse her of trolling for a date, but no one exactly congratulated her on the outfit either. (Or glance at the wardrobes of such titans as Meg Whitman, who just stepped down from her post as eBay's C.E.O., and Irene Rosenfeld, head of Kraft Foods. For them, the way to success was brains, hard work, and separates from Talbots.)

There are, of course, the rare exceptions to the rule. Julie Macklowe, portfolio manager for Sigma Capital Management, was recently recognized as an "It" girl by Vogue. And, speaking of that venerable title, fashion is perhaps the one industry where showing up looking like a slob or like a buttoned-up matron can get you into hot water. Don something less-than and you could face the same question: "Who has time for…that?"