5 Summer Trends That Anna Wintour Predicted 20 Years Ago

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 demeanour 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 bold neon dresses and silky slip skirts, scroll down to see some of young Anna Wintour’s chicest looks that are trending with fashion girls over 20 years later.

Leopard Print

THEN: From her leopard-printed coats to ridiculously chic frocks, Anna propelled the animal print to new heights.

NOW: Leopard print is now ubiquitous and we're certain that's thanks to Wintour's love of the pattern. Fashion girls everywhere still love it in a slip dress or slip skirt as seen on the Insta set around the globe.


THEN: Polka dots were initially made fashionable by Christian Dior, and Anna Wintour knew that this print has always been a classic and elegant look.

Barely There Strappy Sandals

THEN: The Vogue U.S. 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 favourite fashion muses are loving the barely there strappy sandal trend this summer—as seen all over our Instagram feeds. 

Slip Skirt

THEN: Anna Wintour put the versatile silvery slip skirt on the map.

NOW: Today, the style set is giving a modern take on the versatile slip skirt by pairing it with a sweater and heels or boots. 


THEN: Neon was a bold choice, but as usual, Wintour makes this look chic by opting for the trend in a shift dress.

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