Photos of RuPaul Through the Years

RuPaul is arguably the most famous drag queen in the world, and as the creator of RuPaul’s Drag Race, has literally paved the way for future drag superstars. But RuPaul Charles isn’t just a fashion queen, he’s written books, songs, hosted talk shows, had acting gigs on multiple TV shows, including his own short-lived Netflix show AJ and the Queen and of course his role as host and producer of Drag Race. Somehow this multi-talented superstar still finds time to look amazing every single time he steps out of the house. No matter if it’s in a tight, super-short slinky dress, a beaded ballgown or a smashing suit, the look is always going to be fabulous. We’ve rounded up some of the glamazon’s most memorable and iconic looks from the past. So sashay your way through this gallery and get ready for some retro fun.

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RuPaul has famously been quoted saying: “We’re all born naked and the rest is drag.” This stripped down look from his youth really was the blank slate for some of the amazing drag looks to come.

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In full party girl mode at NYC’s Roxy nightclub.

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Ru doing a Foxy Brown look. Check out those boots!

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Right before Ru’s hit song “Supermodel (You Better Work)” rocked the charts, she posed right in the middle of NYC’s Times Square.

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Love this little (and we mean little!) black dress.

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RuPaul sported this super patriotic one-piece look at the Gay Rights March in April 1993.

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RuPaul has made a lot of celebrity friends, here is Ru hamming it up with the late, great comedienne Joan Rivers.

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Speaking of celebrities, peep Ru surrounded by Kurt Cobain, Krist Novoselic and Dave Grohl of Nirvana.

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You know you’ve hit iconic status when you are performing with Sir Elton John. Here RuPaul and Elton are rocking the Brit Awards.

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Forget those Victoria Secret Angels, RuPaul owned the winged look at the VH1 Fashion And Music Awards.

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Another gold dress, but if something works, why change it? Plus, this mermaid-seaweed coat is an unforgettable touch.

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RuPaul with Anna Nicole Smith are twinning in anything but basic little black dresses.

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Michelle Visage would have a field day poking fun at this wig if it was on a Drag Race contestant, but to be fair, this look was from one of Ru’s acting gigs during a guest spot on Nash Bridges.

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Love this stripped down look with a rather tame leopard hat for the Sundance Film Festival.

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If you are going to pay tribute to Diana Ross, you better show up looking over-the-top amazing, and RuPaul hit that challenge out of the park. This VH1 Divas 2000 ensemble had gold, glitter, features and a massive lioness wig.

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More gold in this glam cowboy look for Wigstock. That tiny waist is to die for.

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In the last decade or so, RuPaul has most often been spotted on the red carpets (or in this case blue) wearing some perfectly tailored suits, and this pattern mix is spot on.

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At the Fashion Does Drag Ball, Ru went for a more streetwear male drag, which, of course, he nailed.

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And while his public looks now are mostly suits, you can still see Ru in drop dead drag and wigs weekly (like this black and white number) on the runway of RuPaul’s Drag Race.

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Ru is no shrinking wall flower in this foliage-like suit at the Variety And Women In Film’s 2018 Pre-Emmy Celebration.

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Ru looked phenomenal in this hot pink, zebra-striped suit, with some feathers and sparkle for the last Met Gala pre-pandemic shutdown.

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