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.
THEN: From her leopard-print coats to ridiculously chic frocks, Anna propelled the animal print to new heights.
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.
Barely There Strappy Sandals
THEN: The Vogue editor in chief has been wearing the same style of neutral (Manolo Blahnik) strappy slingback sandals since the ’90s. The versatile shoes will simply never go out of style.
NOW: Our favorite fashion muses are loving the barely there strappy sandal trend this summer—as seen all over our Instagram feeds.
Slip Dress/Slip Skirt
THEN: The fashion legend has been an advocate of all things silky, slinky, and slip since her early years. Today, we’re still completely on board.
THEN: Anna Wintour put the versatile silvery slip skirt on the map.
NOW: Today, the style set is giving the versatile slip skirt a casual touch—pairing it with tees, sneakers, and sweaters.
THEN: Statement buttons added a sophisticated touch to Anna Wintour’s outfits.
NOW: The button trend has dominated this season, adorning the tops and dresses of our favorite street style stars. Thanks for the inspo, Anna!
Available in sizes S to M.
This post was published at an earlier date and has been updated by Judith Jones.