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.
Shop Anna Wintour's Look
Shop Princess Diana's Look
Next up, this is the only boot trend that matters, according to Anna Wintour.
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It's True: Julia Roberts Just Brought Back Princess Diana's Favorite $70 SneakersShe just landed in Venice, Italy.
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Kim Kardashian Just Wore Princess Diana's Necklace—Here's the Full Backstory on the Royal JewelIt has a fascinating history.
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I Live in Venice Beach, Where Low-Key Style Is It—These Outfits HitThe living is easy.
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Taylor Swift Just Wore Princess Diana's Signature Off-Duty UniformChic.
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Princess Diana's $90 Pink Sneakers Are as Cool as Ever in 2023Timeless.
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H&M's New $20 Shoes Look Just Like Anna Wintour's and Princess Kate's VersionsQueen Letizia is also a fan of this shoe trend.
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Anna Wintour Only Packed One Shoe Trend for All of Fashion MonthSo in vogue, obviously.
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These New Zara Jackets Are Giving Major Princess Diana VibesDon't you agree?
