For many women, picking the perfect outfit for an occasion can be extremely stressful -- something 29-year-old Jess knows all too well. "You want to look cute when you have to be cute," she says, "but you need to be sophisticated and professional when that calls for it as well. I'm worried that my clothes are sometimes giving off the wrong message in these different situations." But with all the attention women pay to choosing just the right look, do guys really even notice? Rach's buddy Colby Donaldson says absolutely. "It's about sending signals," he confirms. "You are sending signals, so it's just about determining what those signals are going to be." Colby sits down with three average guys to talk about what men really think about the way women dress.

Colby's bottom line? "I think the message for all women," he says, "is to determine what message you want to send, whether that's conservative or whether that's sexy or casual. Once you determine that, the only way you're going to pull that off is confidence. It's got to be something you're comfortable in. When we were watching this on TV as a group of guys and Jessica came out in her Saturday-night-sexy outfit, she jumped off the screen and everyone was like, 'Wow, that's sexy!' And it wasn't even about her outfit. It was how confident she was. She owned it."