Your girlfriend’s out of town? Wow, thanks for telling me—and everyone else on the street—right there on your T-shirt. You may not even have a girlfriend, but that ironic slogan sure is selling your desirability. Too bad nobody’s buying it.

Thinking of shelling out for a message tee? You might want to consider carefully what it will say about you. Are you sure the world needs to know that you have MORNING WOOD, that you’re TALENTLESS BUT CONNECTED, or maybe even a CULT MEMBER? Perhaps there was a time, like last November, when you felt the choice was VOTE OR DIE, but Kerry lost.

“I only notice them if they’re stupid, like MY GIRLFRIEND’S OUT OF TOWN,” says Amy Sacco, owner of New York nightclub Bungalow 8. “And there are plenty of stupid T-shirts. I really don’t need to see Vinnie So-and-So walking down the street saying AVAILABLE.” Indeed. A T-shirt that talks is a desperate bid for attention. “Someone who is really confident in who they are doesn’t need that kind of advertisement,” says Todd Snyder, vice president of men’s design at J. Crew. But for some people who can’t get their own billboard on Sunset, their body is the next best thing. “The last one I saw was this young man in my store in a T-shirt that said I’M OUT OF BED. I’M DRESSED. WHAT MORE DO YOU WANT?,” says retailer Jeffrey Kalinsky. “If I like the message, I’m for them. But not if they say something like 100% PRIME MEAT.”

That’s the point: As Spinal Tap taught us, “there’s a fine line between stupid and clever.” And too many guys have no clue where it is. “Slogan T-shirts are supposed to be about self-expression,” says Robert Burke, senior vice president of fashion and public relations at Bergdorf Goodman. The problem, he explains, is that if you’re expressing yourself the same way as that other guy—make that 5,000 other guys—that’s not terribly expressive. “You don’t want to see it coming and going,” he says. After all, how many men really get LUCKY IN KENTUCKY?

So what motivates a man to cover his chest with cheese? Young Hollywood is partly to blame—Ashton Kutcher and Ben Affleck have both advertised that Jesus is their homeboy. (It’s a matter of time before Rick Salomon is seen sporting a BIG DICK.) “It depends on what T-shirt you’re wearing, and who you are,” says publicist Lara Shriftman, noting, “Brad Pitt can get away with it, Billy Bob Thornton can get away with it.” You, unfortunately, cannot.

It’s hard to remember that the original message of slogan T-shirts was one of rebellion—and if you bought yours for $88 at Barneys, you don’t have a lot to rage against. “If you’re going to be rebellious,” says Burke, “you have to be unique.” And don’t even think of throwing your tee over a long-sleeve shirt to show your unstudied layering savvy—nothing looks more mixed up. At this point, the best way to stay on message is to tuck in a beat-up Oxford, keep your thoughts to yourself, and stop trying so hard. “A slogan T-shirt can be like a bad haircut,” warns Kalinsky. “People might not know what to say, so they’ll say ‘Hey, love your T-shirt.’” But what’s more likely is that when it comes to the people you most want to talk to, you’re ending the conversation before it even begins.