Simpson-Wentz the trendsetter. This chic chocolate shag hairstyle was "The Rachel" of its day. It inspired copycats around the world at the time and continues to do so now.

Rinna took what has to be the most famous and popular haircut in recent memory (yes, even more copied than "The Rachel"), and turned it into something you might see during Bingo night at a resort in the Poconos. Lesson: don't mess with perfection.

This breezy haircut not only looks great on Rinna, it looks great on everyone (and there's a lot of them) who wears it. The epitome of low-maintenance, this shag allows Rinna's stunning features to take center stage.

Can't you just picture it? It's a big red carpet event day for Milano, and her stylist suggests they do something different with her hairstyle. By the time they realize it's a hot mess, the limo has arrived, and Milano has to go. We've all been there.

While we like her little pixie short hairstyle, with long hair Milano really embodies the ideal of the classic Italian beauty. This style with its carefree waves looks great pulled off the forehead to showcase Milano's gorgeous face.