Anna Wintour Puts on Perhaps Her Most Important Dress Ever

In 1988.

In 1989.

In 1990 with Donna Karan, for Theatre de la Mode.

In 1993, with Calvin Klein and Si Newhouse, for Diana Vreeland: Immoderate Style.

In 1994.

In 1997 with Andre Leon Talley for the Costume Institute's tribute to Gianni Versace.

In 1999 with Elizabeth Hurley for Rock Style

In 2003, wearing Christian Dior couture, for Goddess.

In 2003, wearing Christian Dior haute couture, for Goddess.

In 2004, wearing Christian Dior couture for Dangerous Liasons: The Art of Seduction.

In 2005, wearing Chanel couture with Shelby Bryan, for Celebrating Chanel.

In 2006, wearing Christian Dior couture, for Anglomania.

In 2007, wearing Chanel couture, for Poiret: King of Fashion.

In 2008, wearing Chanel couture for Superheroes: Fashion and Fantasy.

In 2009, wearing Chanel couture, for The Model as Muse: Embodying Fashion.

In 2010, wearing Chanel couture, for American Woman: Fashioning a National Identity.

In 2011, wearing Spring 2011 Chanel couture, for Alexander McQueen: Savage Beauty.

In 2012, wearing custom Prada, for Impossible Conversations: Schiaparelli and Prada.

In 2013, wearing custom Spring 2013 Chanel Couture, for Punk: Chaos to Couture.

In 2014, wearing a gown with sheer fabric at the neck and shoulders, for Charles James: Beyond Fashion.