How about if she's wearing too much makeup or unflattering clothing? Faith says that can be tricky, and it might be a good idea not to bring it up. "I think that's a form of self-expression, and they're going to feel bad about themselves—especially someone who's overweight," she says. "I think that could do a lot of damage to their self-esteem."
Randy agrees that you shouldn't be offering any advice—unless a friend specifically asks for it—in matters of taste. "Ask yourself this: Does my friend own a mirror? Has my friend employed me as her fashion consultant? Otherwise, I wouldn't volunteer," he says. "She knows how she looks. If she chooses to look that way, she's allowed to."