Today we take a break from our regularly scheduled programming of judging specific Met Galas, and instead choose to rate one specific person’s outfits in honor of her recent birthday on Nov. 3. Dame Anna Wintour, I wish you the happiest of birthdays; please enjoy a ranking of some of your best Met Gala looks to date.
One of Wintour’s best Met looks occurred at 2015’s gala, with the theme “China: Through the Looking Glass.” Wintour wore a stunning Chanel dress decorated with hundreds of red flowers. Accompanied by her daughter in a burgundy Alexander McQueen dress embroidered with cherry blossoms, the duo looked fabulous. Similarly, Wintour also wholly embodied the theme at the 2018’s “Heavenly Bodies” gala, where she stuck with Chanel, looking beautiful in an all-white, short-sleeved gown accessorized with an eye-catching diamond rosary.
Wintour has a close relationship with Chanel and frequently wears their designs to the Gala, and they are frequently show stealers. For one of Wintour’s most iconic looks, search no further than her 2008 Chanel look for “Superheroes: Fashion and Fantasy.” Wintour looked like a futuristic supervillain in a silver gown, which took inspiration from the X-Men character Storm. This outfit was heavily criticized at the time, with some calling it the “worst fashion faux pas,” however, I fully believe Wintour did an incredible job at delivering a unique look while adhering to the theme.
Despite being chairwoman of the Met Gala, Wintour does not always stick to the theme and occasionally wears very off-theme looks, but this does not mean they are necessarily bad. For the 2013 “Punk: Chaos to Couture” gala, Wintour wore yet another floral Chanel gown. The dress was colorful and elegant, however, it did not match the theme. In all honesty, this is one of the few Met Galas where Wintour’s look felt out of place. For the most part, Wintour does a solid job of coinciding with the theme.
Now, before I reveal the top two Wintour Met Gala looks, we must address one of her most disappointing looks. Considering her close relationship with Chanel, the 2005 House of Chanel gala should have been an easy theme for the fashion icon. Sadly, Wintour’s look was subpar. She wore a white gown with a white intricately embellished jacket and a pearl necklace. The look was not bad, it just could have been so much better and I expected more from someone who wears so much Chanel.
The two best Wintour Met looks come from her early years as chairwoman. In 1996 for the “Christian Dior” gala, Wintour wore a simple yet beautiful spaghetti-strap dress with a blue and white floral pattern. She accessorized with her iconic sunglasses and a magnificent orange jeweled necklace. Wintour’s best look, though, has to be her outfit from the 1997 “Gianni Versace” gala. In a sleek silver dress and long black coat with a magenta fur collar, Wintour truly established herself as a Met Gala icon and the epitome of elegance and style, which was of course emphasized by her classic sunglasses.
