Isabel Cafaro, executive assistant
"I was twelve, just starting middle school, and every girl was wearing lipstick. Remember the back-in-the-nineties, dark lipliner/nude lip combo? Yeah, that was happening. And it had to be MAC. Of course, like every middle schooler, I wanted to fit in, so I begged my Mom to buy me that MAC Spice Lipstick and Chestnut Lipliner everyone was wearing. I needed it, I wanted it, I yearned for it, and I got it -- at 15 bucks a pop. That was my first big makeup spurge and they've only gotten pricier ever since. At least, now, I spend my own dollars instead of my Mom's."

MAC spice lipstick, $14.99, available on eBay.