Princess Diana and Anna Wintour Wore Your Dream Party Outfits in '96

Today in unlikely pairings: Princess Diana and Anna Wintour were apparently friends back in the '90s. The icons attended a fundraising event for breast cancer research in Washington, DC, in 1996 and were the epitome of class in their contrasting black and white gowns, respectively. Oh, and none other than Ralph Lauren joined them—imagine being seated at that table.

The late Lady Di stunned in a white lace column gown that could easily pass as a wedding dress, along with matching white pumps with crisscross straps. The perennially chic Anna Wintour was the yin to the princess's yang in a one-shoulder black gown and coordinating pointy-toe pumps. With plenty of holiday parties on the horizon, who better to look to for outfit inspiration than these two fashion powerhouses? Scroll down to see their timeless '90s looks and to shop the trends for 2019 and beyond.


(Image credit: Getty Images)


(Image credit: Getty Images)

Shop Anna Wintour's Look

Shop Princess Diana's Look

Next up, this is the only boot trend that matters, according to Anna Wintour.

Associate Director, Fashion News

Erin got her start as a Who What Wear intern over 12 years ago—back when the site only published a single story per day. (Who What Wear has since increased that number twentyfold.) She graduated magna cum laude from USC, which is how she ended up moving to Los Angeles from her hometown of San Diego. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2016, where she currently holds the title of Associate Director of Fashion News (as well as the unofficial title of resident royal expert—in case you haven't noticed her numerous Meghan Markle and Kate Middleton stories). She spends her days trying to incorporate her idols, Anna Wintour and Roger Federer, into as many stories as possible. Outside of work, she loves tennis, classic rock, traveling, and smothering her dog with affection.