There have been many first Mondays in May.
As we prepare for yet another Met Gala next week, it’s easy to forget how much fashion—and the famous people that rock it—has changed. Much like the the annual fundraising gala itself, the styles and stars have evolved with the times. As the event has grown from a New York-centric soirée to a glitzy Hollywood bash, the ensembles have equally expanded in creativity and panache.
After 46 years in existence, countless gowns have made their way up the iconic red-carpeted staircase, cemented in the annals of fashion thanks to the throngs of photographers standing by.
It is because of those photographers that we can look back on years worth of Met Gala appearances from Hollywood’s reigning fashionistas. From longtime attendee Naomi Campbell to chairwoman Anna Wintour, here are all of your favorite style icons’ first gala appearances paired with their most recent one. Let the time traveling begin!
Raymond Hall/GC Images/Ron Galella/WireImage
Let’s begin with the woman of the ball herself, Vogue’s Editor-in-Chief and the Met Gala’s ringleader. She arrived at the event for the first time in 1989, sporting a gold blouse, black skirt and her signature bob. Fast forward nearly three decades later, the magazine maven made even more of a statement as she posed in a fringe gown by Chanel.
Karwai Tang/WireImage/Gucci via Getty Images
The Oscar winner has been quite the fashion chameleon in the course of her accomplished movie star career and her Met Gala looks are indicative of that evolution. In 2003, she donned a sparkling one-shoulder gown with elaborate chandelier earrings. However, the black tie look seems rather reserved when compared to the caped and plunging Alexander McQueen number she sported last year.
Taylor Hill/FilmMagic/Kevin Mazur/Getty Images
Sarah Jessica Parker
While the ever stylish Parker can always be counted on to push the boundaries of fashion with her sartorial twists, she played it unexpectedly safe for her first turn down the Met Gala carpet in 1995 in a simple velvet gown. Fast forward to her 2016 Monse tailored jacket with ruffled sleeves—less Carrie Bradshaw, more signature SJP.
Dimitrios Kambouris/Getty Images/Ron Galella/WireImage
Having been in the business for decades, the iconic supermodel has flaunted an array of looks at the Met Gala, beginning with this multi-colored mini at the 1990 event. By the time 2016 hit, Campbell had extended the hem in this floor-length beaded and cut-out gown by Cavalli Couture.
Richard Young/REX/Shutterstock/Ron Galella/WireImage
Whether it’s 1990 or 2012, the forever ’90s cool girl seems to always have one key accessory with her on the Met Gala red carpet—her bangs! Still, if you were to look up 1990 in the dictionary, a photo of Tyler’s first appearance would definitely pop up.
Stephen Lovekin/Getty Images/George Pimentel/WireImage
The Grammy winner may also be one of the biggest toasts at the Met Gala whenever she attends, but when it comes to taking risks, it seems the star has gotten more comfortable stepping out of the box as the years have progressed. In 2008, she opted for a reserved powder pink strapless gown with a ruffle down the side. The look was pretty in pink, but by 2016, the songstress donned a similar shade in latex Givenchy and a bold smokey eye to boot. That’s the way to push the envelope!
CHANCE YEH/Patrick McMullan/George Pimentel/WireImage
On the heels of her breakthrough studio album, the Grammy nominee sported a vibrant blue gown for her first Met Gala strut. Two more albums and seven years later, Perry became the gala’s resident risk-taker in a standout Moschino gown and Marge Simpson-inspired ‘do.
George Pimentel/WireImage/Larry Busacca/Getty Images
The Material Girl can always be counted on to make a stylish splash, whether it’s 2009 and she has an elaborate hair accessory on her head or it’s 2016 and she’s in sheer Givenchy.
Dimitrios Kambouris/WireImage/Taylor Hill/Getty Images
While it’s been more than a decade since the actress’ first Met Gala attendance, she’s clearly stayed true to her signature aesthetic in sharp and clean silhouettes, albeit a touch sweeter in 2003 and a bit more bold in 2016.