When Sacha Baron Cohen crashed a runway show in Milan back in 2008 disguised as Brüno, his Austrian alter ego, the audience barely blinked. Dressed in an absurd Beyond Thunderdome pastiche of layered fabrics and dangling tassels, the comedian emerged onto the catwalk with an expertly executed strut. It was only after security stormed the stage and escorted him away that most spectators realized they'd been had.

If industry cognoscenti have a hard time distinguishing between fashion coup and fashion joke, it's easy to see how a mere civilian can, with just a few daring wardrobe choices, stumble into punch-line territory. Extreme style infractions are less forgivable in men than they are in women: Since they have fewer opportunities to blunder, guys must almost willfully court catastrophe. Train-wreck dressing isn't all about egregious misjudgments, like showing up at work in Boy Scout shorts. Even the simplest misstep can make you look like an asshole: white plastic sunglasses, an "It" man bag, or a scarf worn indoors. The well-dressed man knows his limits, and though he might occasionally test them, he never attempts to make a statement he can't back up.

Sure, there are guys who can pull off a madras-shirt/bow-tie combo or oversize Elvis Costello frames, but for every man who manages to look cool in a cowboy hat and chaps there are a thousand who'd look like rodeo clowns. Clothes can be transformative, but they have to correspond to your personality. You know you've spotted a fashion victim when you notice what a man is wearing—those metallic patchwork high-tops, the skinny-fit women's jeans—before you notice the man himself.

"A fashion victim is literally a slave to fashion," says Tom Ford, who has seen his fair share of casualties during his 25-plus years in the business. "The clothes wear him instead of the other way around." Dean Caten of Dsquared takes it a step further, seeing victims as junkies fiending for the latest fad. "Addicts overdose," he says.

There are degrees of victimhood. The least offensive is probably the Logo Whore, the guy whose self-esteem is pegged to the number of designer labels he's promoting. Next in line is the Mannequin Mimic, who dresses from head to toe in a single brand. Still worse is the Character Actor, whose wardrobe is based on a theme, whether it be nautical or early Bowie. And finally, there's the VMAN Subscriber, the fashion devotee who is always trending. Right now he's most likely wearing a shawl-collar cardigan, a quilted vest, two-tone wing tips, electric-blue jeans, and a gaggle of Thai bead bracelets. "He has to have it all at one time," says Dan Caten, the other half of Dsquared, "and it doesn't make any sense."