Fashion icon Anna Wintour is synonymous with classic style—from her pearl statement necklaces to her tweed skirt suits and those signature black Chanel sunglasses—her chic demeanor is unmistakable. Yet while there have always been elements of timeless pieces in her repertoire, the Vogue editor in chief’s earliest style moments are surprisingly bold. She has unquestionably inspired some of today’s biggest trends. From fearless leopard print to rainbow sequins and silky slip dresses, scroll below to see some of young Anna Winter’s chicest looks that are trending with fashion girls over 20 years later.
NOW: Today, the style set is giving the versatile slip skirt a casual touch—pairing it with tees, sneakers, and sweaters.
This post was published at an earlier date and has been updated by Judith Jones.