The Wintour Position: 21 Years of Anna Wintour U.S. Open Candids
Anna Wintour will attend the U.S. Open. She is more likely to sit in the stands, close to the court, than in a box. She will wear a tailored midi dress in colorful, patterned silk. If it is sleeveless (which is likely), she will bring a cardigan. She may not remove her sunglasses, but she will cheer and sometimes smile. Her outfits change. Her silhouette does not. Her companions change, though many recur.
When Wintour announced last June that she was handing off the day-to-day editing of American Vogue, she told her staff she planned to remain Vogue’s tennis and theater editor in perpetuity. It was a joke with a paper trail.
The woman who spent 37 years dictating the fashion industry’s ups, downs, ins and outs has herself gone remarkably unrevised. Wintour knew who she was before most of the industry’s current leadership had a first job, and she has not revisited that conclusion. Consistency is her brand, and it is legible. At the U.S. Open, it is measurable—the same tournament, the same week, the same seat, across 21 years of candids.
What do decades of discipline and consistency produce? The Wintour Position.
2005, Day 10, Quarterfinals.

2005, Day 14. Men’s Final, Andre Agassi vs. Roger Federer with Donald Trump.

2006, Day 10.

2006, Day 13. Men’s Semifinal, Roger Federer vs. Nikolay Davydenko, with Mirka Federer.

2007 Opening Ceremonies, credentials doubled around the neck.

2007, Day 14. Men’s Final, Roger Federer vs. Novak Djokovic.

2008, Day 1. With Oscar de la Renta, who would occupy the adjacent seat for the better part of five years.

2009, Day 3. Roger Federer vs. Simon Greul.

2009, Day 8 with Tony Godsick, Oscar de la Renta and Mirka Federer.

2009, Day 14. Rafael Nadal vs. Juan Martin Del Potro.

2010, Day 10. Men’s Singles Quarterfinals, Roger Federer vs. Robin Soderling with Mirka Federer.

2011, Day 1. Roger Federer vs. Santiago Giraldo.

2011, Day 15. Men’s Final, Novak Djokovic vs. Rafael Nadal.

2012, Day 8 with Shelby Bryan.

2012, Day 10.

2012, Day 13. Andy Murray vs. Tomas Berdych.

2013, Day 1. Sunglasses Off.

2013, Day 14. Sunglasses On.

2013, Day 15. Men’s Singles Final Match, Novak Djokovic vs. Rafael Nadal with Shelby Bryan.

2014, Day 1.

2014, Day 2. Roger Federer vs. Marinko Matosevic.

2014, Day 5. Federer’s box with Vera Wang.

2014, Day 11. Roger Federer vs. Gaël Monfils with Hugh Jackman.

2014, Day 13. Men’s Singles Semifinals, Roger Federer vs. Marin Cilic with Shelby Bryan.

2014, Day 5. Men’s Singles Quarterfinals, Roger Federer vs. Gaël Monfils.

2015, Opening Day with daughter Bee Shaffer.

2015, Day 2. Sunglasses secured for Andy Murray vs. Nick Kyrgios.

2015, Day 9. Women’s Singles Quarterfinals, Serena vs. Venus.

2015, Day 10 with Shelby Bryan and Mirka Federer.

2015, Day 14. Men’s Singles Final, Roger Federer vs. Novak Djokovic with David Beckham.

2016, Day 1. Men’s Singles, Novak Djokovic vs. Jerzy Janowicz with Vera Wang.

2016, Day 8. Fourth-Round Women’s Singles, Venus Williams vs. Karolina Pliskova.

2016, Day 12. Men’s Semifinal, Novak Djokovic vs. Gaël Monfils, with Jelena Djokovic.

2017, Day 12.

2018, Opening Night. Sunglasses off with Wendi Deng Murdoch.

2018, Day 2. Federer’s match in Federer’s box. Sunglasses on with son, Charles Shaffer.

2018, Day 3. Serena Williams’ box.

2018, Day 4. Back to Federer’s box for Federer’s match.

2019 Finals.

2020. The Open was played without spectators.
2022 Men’s Singles Finals, Carlos Alcaraz vs. Casper Ruud, with Huma Abedin.

2022, Day 3. Women’s Singles Second Round, Anett Kontaveit vs. Serena Williams.

2023, Opening Day with Vera Wang. The brace is new.

2023, Day 3. Men’s Singles Third Round, Alejandro Davidovich Fokina vs. Tommy Paul with Huma Abedin.

2023 with Emma Watson.

2023.

2023.

2024, Opening Day with Vera Wang.

2024, Day 2.

2024, Day 3. Men’s Singles Second Round.

2024, Day 8. Women’s Singles Fourth Round, Caroline Wozniacki vs. Beatriz Haddad Maia.

2024, Day 12 with David Duchovny and his daughter, West.

2024, Women’s Final, Aryna Sabalenka vs. Jessica Pegula, with Lewis Hamilton.

2024, Day 14. Men’s Singles Final, Jannik Sinner vs. Taylor Fritz with Eddie Redmayne.

2025, Day 4 with James Corden.

2025, Day 9. Men’s Singles, Felix Auger-Aliassime vs. Andrey Rublev, with Rami Malek.

2025, Day 13. Men’s Singles Semifinal, Felix Auger-Aliassime vs. Jannik Sinner, with Hugh Jackman.

2026 with Serena Williams.

2026, Day 2.

2026, Day 5. Women’s Singles Second Round, Coco Gauff vs. Paula Badosa with Michael Kors. A designer in the adjacent seat, 18 years later.

