The star wore Calvin Klein to her inaugural – and most recent – Met Galas.
The artist formerly known as Puff Daddy found out what happened “if you had J.Lo’s love” in 1999: He got an invite to squire her to a fancy gala in matching neutral-colored ensembles.
A lady who knows a thing or two about good jewels, Princess Diana accompanied her fashion editor friend Liz Tilberis (and outshone the celebs) in a Dior gown and her famous pearl-and-sapphire necklace.
Who better than the former Posh Spice to represent the U.K. in a regal red tea-length dress for the AngloMania year?
Jessica’s interpretation on the Jacqueline Kennedy theme that year was a decidedly beachy one.
Even at an exhibit dedicated to one of the most flamboyant designers of all time (Gianni Versace), Sandra is going to do Sandra – and we love her for it.
It’s a tribute to the star’s enduring fashion icon status that she could wear this exact dress on Monday and we wouldn’t bat an eye.
It takes a true supermodel to outshine a dress so sparkly, it’s practically galactic. Naomi Campbell is that supermodel.
Ivanka had a very busy May that year: Not only did she attend the Met Gala in a butterfly appliqué column, she graduated from the University of Pennsylvania cum laude.
Drew’s ability to rock a red lip like no other definitely set the stage for her turn as a makeup mogul a few years later.
It’s a bold star who chooses a mini for the Met Gala, but Kate has never played it safe – even on the biggest red carpet of the year.
The theme was AngloMania, which should help put Eva’s sexy tribute to Jane Austen novels in context.
Once again, Queen Cate proves she can look transcendent in gowns mere mortals can’t even approach.
Between Jake’s rumpled, tie-free suit and Kirsten’s knit beanie, we’re wondering if they thought got their invites mixed up and wore their Hipster Dance Party outfits instead?
And we love this dress – even more for finding out that the year she wore this creation, she had to sit “and let someone else shove the dress in the car,” as she told PeopleStyle at a First Monday in May screening.
The best part of this gorgeous red gown with its cape-like train? She could totally recycle it the next year for the Superheroes theme.
Should the need arise, Melania could recycle this corseted and bustled gown for an inaugural ball.
Their relationship may have lost its magic, but the photos of them from this era (is that a scrunchie?) sure didn’t.
Long before Fashion Faceoffs were a thing, Donatella gave us all a preview of the dress Jennifer Lopez would make immortal at the Grammys the next year.
Another relationship that fizzled, but we will always have the memories of what black tie looks like when you’re Marilyn Manson.
Allover gold sequins never go out of style, but no one makes them look quite as timeless as the news anchor.
Brandy’s shimmery two-piece mini suit with matching silver boots at the Haute Couture-themed event was so fab, it might have been the inspiration for the costumes on Xenon: Girl of the 21st Century.
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