Anna Wintour in The September Issue (2009)

Karl Lagerfeld, Anna Wintour, and Bee Shaffer in The September Issue (2009)

Anna Wintour in The First Monday in May (2016)

Anna Wintour, Wendi Murdoch, and Andrew Bolton in The First Monday in May (2016)

Diane von Fürstenberg, Anna Wintour, Marcus Wainwright, Jenna Lyons, Ken Downing, Steven Kolb, Andrew Rosen, David Neville, Mark Holgate, Jeffrey Kalinsky, and Reed Krakoff in The Fashion Fund (2014)

Diane von Fürstenberg, Anna Wintour, Marcus Wainwright, Jenna Lyons, Ken Downing, Steven Kolb, Phil Winser, Andrew Rosen, Matt Baldwin, David Neville, Mark Holgate, Jeffrey Kalinsky, and Reed Krakoff in The Fashion Fund (2014)

Diane von Fürstenberg, Anna Wintour, Sophie Oakley, and Becca McCharen in The Fashion Fund (2014)

Diane von Fürstenberg, Anna Wintour, Steven Kolb, Andrew Rosen, Mark Holgate, and Jeffrey Kalinsky in The Fashion Fund (2014)

Ye, Anna Wintour, and Kim Kardashian in The Fashion Fund (2014)

Diane von Fürstenberg, Anna Wintour, Jenna Lyons, Ken Downing, Steven Kolb, and Romee Strijd in The Fashion Fund (2014)

Ye, Anna Wintour, and Ken Downing in The Fashion Fund (2014)

Diane von Fürstenberg, Anna Wintour, Jenna Lyons, Ken Downing, Steven Kolb, and Mark Holgate in The Fashion Fund (2014)

Diane von Fürstenberg, Anna Wintour, and Justine Skye in The Fashion Fund (2014)

Diane von Fürstenberg, Amanda Seyfried, Anna Wintour, Steven Kolb, Aurora James, Rio Uribe, and Jonathan Simkhai in The Fashion Fund (2014)

Ye and Anna Wintour in The Fashion Fund (2014)

James Corden, Zac Posen, and Anna Wintour in The Late Late Show with James Corden (2015)

Anna Wintour in Late Night with Seth Meyers (2014)

Sienna Miller and Anna Wintour at an event for Factory Girl (2006)

Anna Wintour at an event for The Oscars (2015)