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.