I'm not sure that there could actually be a style more classic than a bob. Always elegant and decidedly chic, this simple hairstyle is made famous by A-listers like Anna Wintour and Alexa Chung. Yes, it does require a bit of upkeep, as you'll need to get your hair trimmed every four to six weeks, but you'll always look polished and pulled together with this classic hairstyle—whether you wear it tousled, straight or blow-dried for extra volume.