For the better part of a decade, fashion houses have treated men as the new women. They've built them their own boutiques and encouraged them to play with jacket lengths, patterns, and even jewelry. But with all that choice comes a greater potential for error.

There are those who believe there's no such thing as a bad sartorial decision. "If you love what you're wearing and you're enjoying it, that's really all that matters," says Simon Doonan, creative director of Barneys New York. Sadly, that doesn't apply in all cases: Fashion sense might be subjective, but only to a certain point. Embracing seasonal fads is often the first step in a journey that ends with bondage trousers and a jauntily doffed fedora. Men who adhere to the classic and timeless can stay current without having to make risky leaps into the abyss. "Let one thing you're wearing speak," Dan Caten recommends, "and everything else be quiet."

Ironically, the very people who are paid to dispense such style advice often turn out to be the worst offenders. For proof, look no further than Phillip Bloch, the mustachioed stylist-to-the-stars who rolls around L.A. in a backward Kangol hat.

In the end, you can only really trust the guy in the mirror. Ask him if he'd wear the same outfit to brunch with a date, drinks with clients, and a family reunion in Bush country. If he answers no, make him change.

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