Anna Wintour's Younger Style—'90s Style

last updated 13 August 2019

If you think of Anna Wintour’s style today, words such as sheath dress, floral print, and cardigan come to mind. In a word, her look is conservative, which is why we were shocked to see ‘90s-era photos of the now editor-in-chief with a markedly different personal style. While everyone’s look should evolve as they get older, we were quite delighted with a peek at Wintour’s former, more adventurous style spirit.

Scroll down to see photos of a younger Wintour rocking graphic tees, rainbow sequins, and a space-age gold turtleneck.

Anna Wintour at a screening of 'Awakenings.'

Anna Wintour at The Burden Center's 12th Annual Dinner Dance.

Anna Wintour at the Manhattan Center for the VH1/Vogue Fashion Awards.

Anna Wintour and actress Mary Tyler Moore attend the Opening Night Gala and Reception of the 95th Season of the New York City Ballet in 1991.

Anna Wintour in 1993.

Tommy Hilfiger and Anna Wintour during Tommy Hilfiger 'Rock Style' Exhibit at The Metropolitan Museum of Art at Metropolitan Museum of Art.

Anna Wintour at a benefit in 1993

Anna Wintour in 1990

Donna Karan and Anna Wintour.

Are you as surprised as we are that Anna Wintour wore some of these outfits? Let us know in the comments below!

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Kat Collings has over 15 years of experience in the editorial fashion space, largely in digital publishing. She currently leads the vision for editorial content at WhoWhatWear.com as the site's editor in chief, having risen through the editorial ranks after joining the company in 2012. Collings is a Digiday Future Leader Awards nominee, was named Buzzfeed's best fashion Instagram accounts of the year, and is a member of the CFDA Awards Fashion Guild. Prior to Who What Wear, Collings worked on styling projects for brands such as Vogue, Teen Vogue, Lucky, and Oliver Peoples. She graduated from UCLA with a BA in communications and calls Los Angeles home.