It seems as if Anne Hathaway has been portraying the fashion elite for as long as she’s been showing up on our screens. From that epic makeover scene in The Princess Diaries (not to mention the corduroy jacket that launched a million thrifting trips across the country) to The Devil Wears Prada, where she literally plays the gatekeeper to the most influential fashion editor of that fantasy world — and does it all in head-to-toe Chanel. Her transformations, too, have always taken a trajectory from plain to pretty — ditching the flannels, big sweaters, and knee socks for frills, ruffles, and glitter. But as Anne has shown in more recent years — and through complicated, nuanced roles that create a multifaceted image of what being a woman is — there’s more than one way to do pretty.