Anna Wintour Looks

Anna Wintour looked lovely in a long-sleeve floral gown by Marc Jacobs at the 2019 CFDA/Vogue Fashion Fund Awards.

Print Dress

Anna Wintour

Anna Wintour attended the God's Love We Deliver Golden Heart Awards wearing a teal leopard-print gown.

Print Dress

Anna Wintour

Anna Wintour donned a red and black polka-dot dress for the Marc Jacobs Spring 2020 show.

Print Dress

Anna Wintour

Anna Wintour attended the Tom Ford fashion show wearing a blue print dress and her signature Manolo Blahniks.

Print Dress

Anna Wintour

Anna Wintour attended the Vanity Fair 2019 Best Dressed List event wearing her bob, as always.

Bob

Anna Wintour

Anna Wintour attended the 2019 Tony Awards wearing a long-sleeve green print gown by Givenchy.

Print Dress

Anna Wintour

Anna Wintour sported her iconic bob at the 2019 CFDA Fashion Awards.

Bob

Anna Wintour

Anna Wintour looked vibrant in a printed maxi dress with a tiered skirt at the 2019 CFDA Fashion Awards.

Print Dress

Anna Wintour

Underneath her coat, Anna Wintour wore a beautiful beaded column dress, also by Chanel Couture.

Beaded Dress

Anna Wintour

Anna Wintour was stylishly coiffed with her iconic bob, as always, at the 2019 Ellie Awards.

Bob

Anna Wintour

Anna Wintour sat front row at the Michael Kors Fall 2019 show wearing a classic leopard-print coat.

Printed Coat

Anna Wintour

Anna Wintour was spotted at the 2019 Australian Open wearing her signature bob.

Bob

Anna Wintour

Anna Wintour attended the AO Inspirational Series Brunch wearing an ankle-length floral dress with cap sleeves.

Print Dress

Anna Wintour

Anna Wintour added an extra dose of glamour with a tan fur jacket.

Fur Coat

Anna Wintour

Evening Coat

Anna Wintour

Anna Wintour attended the CFDA/Vogue Fashion Fund 15th anniversary event wearing her famous bob.

Bob

Anna Wintour

Anna Wintour was blooming in an ankle-length floral dress at the CFDA/Vogue Fashion Fund 15th anniversary event.

Print Dress

Anna Wintour

Anna Wintour attended the 2018 Golden Heart Awards wearing her signature bob and shades.

Bob

Anna Wintour

Anna Wintour was chic, as always, in a black-and-white flower-appliqued dress at the 2018 Golden Heart Awards.

Evening Dress

Anna Wintour

Anna Wintour sat front row at the Michael Kors Spring 2019 show wearing a striped gray midi dress.

Print Dress

Anna Wintour

Anna Wintour donned a colorful floral frock and her signature strappy heels for the Tory Burch Spring 2019 show.

Print Dress

Anna Wintour

Anna Wintour looked lovely in a painterly floral frock at the 'Girls & Boys' Off-Broadway opening night.

Print Dress

Anna Wintour

Anna Wintour attended the 'Girls & Boys' Off-Broadway opening night wearing this bob with wispy bangs.

Bob

Anna Wintour

Anna Wintour looked fun and glam in a yellow sequined gown by Prada at the 2018 Tony Awards.

Sequin Dress

Anna Wintour