Today would have been the late, great Tupac Shakur’s 43rd birthday. Had he not been gunned down at the age of 25, by now he would likely have been one of hip-hop’s elder millionaires, a la Jay-Z or Dr. Dre. But his early passing, morbidly, means a legacy always tinged with the “what-if.” What if he had been around to continue making (non-posthumous) new albums? What if he had survived long enough to patch the west coast/east coast divide?

Here’s another what-if: What if he had lived long enough to keep pushing hip-hop’s fashion boundaries? A look through classic vintage Tupac images shows a guy who wasn’t afraid to flirt with themed outfits or switch between street wear and suits. So far, 1990s nostalgia in mainstream clothing has usually meant ‘90s *rock* nostalgia… But underground scenes have started to bring back ‘90s hip-hop style (basketball shorts, shower sandals, etc., and vintage ‘Pac can provide plenty of inspiration.

(Thug life? More like thong life, amirite?) Okay, not expecting anyone to really copy this style ever, but here’s ‘Pac when he was a member of Digital Underground. Skip the zebra banana hammock, perhaps, but hey—he clearly never skipped leg day, because #quads. Leg day is always in style.

Denim on denim might be worth revisiting. Also, love Rosie Perez’s black-and-white look there. Gemoetrical shapes and contrast are always in.

It’s summer, so all-white looks are technically playing by the rules. Fit is everything—only the bold will go full-on Tupac baggy. The Kangol hat is a nice extra—where did those go?

You know what’s great about this? Tupac was so tough he could show up to an awards show—in this case, the 1993 Minority Picture Awards—dressed as a toddler. And what? That look dares you to clown his overalls. Only the incredibly fashion-forward and secure could pull this of today. Is it you?

Vests. Pac loved them. Can you?

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