As a former Catholic school student , I can tell you that Britney Spears' most iconic music video look is pretty hard to achieve. Her cutesy schoolgirl outfit in "...Baby One More Time" didn't just happen. It takes a lot of time to properly hike up your pleated skirt and position a white blouse just so. But slide on some thigh-highs, add ribbons to your pigtails, and voila! Schoolgirl Britney has arrived to whatever Halloween party is in your iCal, with wine ready in her book bag.