One of our best friends works at a big magazine, and our running joke is her assistant's outfits. The girl is so "ensembley challenged" (thank you, Cher) that she shows up to work in summer's most exposed trends: A giant turban; a babydoll dress so big, it looks like an L.L. Bean tent; white Ray Bans with jewels. "I'm always so fascinated by her faux pas that I find myself staring," confesses my friend, "and so usually, I'll say, 'Oh, I love your outfit' so I can move in and get a closer look." This weekend, we found ourself doing the same thing - at a party with a particularly fake bag, we said, "Ooh, Chanel," just to get closer to the culprit. The girl with the faux was thrilled, and we were secretly screaming inside. That's when we realized, everyone else must do it, too: The clothing compliment that's really the opposite. But how can you stop yourself? And even more important, how can you tell when someone's being sincere when you wear your boldest outfit?