This outfit feels SO 2005 to me; all she needs are some low-rise Rock and Republic jeans with a janky hem because she keeps catching her heels in her pants legs. (Something that happened to me many times back in the day, including once causing me to fall down and literally break my finger.)  Okay, also a Razr flip phone, a Chloe Paddington bag, a huge cup of Starbucks, and a lot of thoughts about Kevin Federline. Then you’re really set.

(Photo by John Lamparski/Getty Images)