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: Leopard print is having a major moment this season and is set to be huge for fall. Fashion girls everywhere still love a Wintour-esque slip dress or slip skirt—like this one—seen on the Insta set around the globe.
THEN: On an evening in 1990, Anna Wintour made a bold statement in a rainbow sequin party dress. Her love of shimmery sequins has been palpable throughout the years—a trend we saw all over the runways this S/S 18.
NOW: It girls (such as Rosie Huntington-Whitely) have been embracing colorful sequins since their revival on the runway this year. Who knew a trend Wintour wore over 20 years ago would be so popular today?