One word can be used to describe Anna Wintour's style: consistent. Having worked in the fashion industry since her teens, she's always had access to incredible clothes, but she's also had the wisdom to steer clear of trends we all laugh about now (okay, some of her shoulder pads in the eighties were a bit much, but whose weren't?). About ten years ago, she abandoned pants entirely and adopted a signature silhouette: a nipped-in waist, a hemline falling to her knee or below, and a conservative neckline, usually accessorized with a chunky necklace. Even though she could probably borrow whatever she wants from designers, she re-wears her favorite pieces often, often choosing colorful prints and pairing them with cream slingback Manolos or an equally simple shoe. Of course, she's not above regular doses of whimsicality — she wore a lobster on her dress to the 2012 Met Gala, for example. Enjoy a look back at her personal style over the years.