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32 Anna Wintour Dresses & Skirts Looks

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 Print Dress

Print Dress

Anna Wintour

Anna Wintour donned a floor-length leaf-print dress by Marc Jacobs for the Fashion Fund finalists celebration.

 Cocktail Dress

Cocktail Dress

Anna Wintour

Anna Wintour donned an elegant blue and black cocktail dress for the Global Fund event.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour stuck to her signature classic lady-like look with this white and red checked A-line frock.

 Knee Length Skirt

Knee Length Skirt

Anna Wintour

Anna Wintour kept her look polished and sophisticated with a printed skirt at the Kimberly Ovitz runway show.

 Beaded Dress

Beaded Dress

Anna Wintour

The queen of 'Vogue' wore this playfully sequined sheath dress to the CFDA Awards.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour donned a crisp taffeta print cocktail dress for the premiere of 'The Whistleblower.' Anna layered a beaded necklace and donned her signature bob for the look.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour looked ageless in a floral Chanel Couture frock during the MoMA film benefit.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour chose a Michael Kors print dress for the Couture Council Fashion Visionary Awards.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour looked sleek and classy in this floral-print floor-length dress, which she wore to the 2013 Met Gala.

 Cocktail Dress

Cocktail Dress

Anna Wintour

Anna Wintour looked lovelier than ever in this drop-waist print dress at the Art + Film Gala.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour surprised us all in this embroidered sheath dress from Versace.

 Print Dress

Print Dress

Anna Wintour

Anna stepped onto the red carpet in a green pleated abstract print dress for the 'Harry Potter' premiere.

 Cocktail Dress

Cocktail Dress

Anna Wintour

Anna Wintour looked very dressy, as always, in a blue Michael Kors cocktail dress with flutter sleeves when she attended the Golden Heart Awards.

 Print Dress

Print Dress

Anna Wintour

Anna kept it classic and chic in a blush pink floral frock.

 Cocktail Dress

Cocktail Dress

Anna Wintour

Anna Wintour's white tweed dress looked sophisticated and polished on the fashion icon.

 Cocktail Dress

Cocktail Dress

Anna Wintour

Anna looked like a doll in this iridescent A-line cocktail dress at the Golden Heart Gala.

 Evening Dress

Evening Dress

Anna Wintour

Anna Wintour wore this dramatic netted dress to the White House State Dinner.

 Knee Length Skirt

Knee Length Skirt

Anna Wintour

Anna donned a high-waisted embroidered knee-length skirt with large pockets to the CFDA Awards.

 Pencil Skirt

Pencil Skirt

Anna Wintour

Anna Wintour looked very ladylike in a floral pencil skirt teamed with a twinset during the Salvatore Ferragamo fashion show.

 Print Dress

Print Dress

Anna Wintour

Anna Wintour wore this pink watercolor dress while out in New York.

 Evening Dress

Evening Dress

Anna Wintour

Anna Wintour looked sleek and elegant as ever when she wore this cream column-style gown.

 Print Dress

Print Dress

Anna Wintour

Anna's printed dress with structural shoulders was a bold choice for Vogue's Editor and Chief.

 Cocktail Dress

Cocktail Dress

Anna Wintour

Anna Wintour wore a blue satin dress with a tiered texture to the Human Rights Campaign Gala.

 Evening Dress

Evening Dress

Anna Wintour

'Vogue' editrix Anna Wintour shone at the 2011 Met Gala in a beaded pastel Chanel gown with black sequined sleeves.

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