We figured as we’d already written a feature on his former-friend-turned-enemy Notorious B.I.G. then it would only be right to do one on the equally trailblazing fashion of Tupac Shakur. Both fans of Versace, both with a penchant for mixing streetwear with haute couture, and both two of the greatest rappers to have ever lived. However both absolute originals in their music and their fashion sense so it’s only right they both get their own dedicated space.
Tupac Amaru Shakur was born to two prominent members of the Black Panther Party a month after his mother was acquitted as part of the famous Panther 21 trial. He was part of a large family of Black Panther activists and this would later feed into his music, his poetry, his outlook. His mother would also struggle with crack cocaine addiction as he grew up in deprived areas in Harlem and Baltimore, this was the 1980s after all and the height of the crack epidemic.
Tupac was clearly well aware of struggle from a young age - the Civil Rights struggle, financial struggles, struggles with addiction - he was surrounded with it from day one. He was also surrounded by culture and would go on to go to attend the Baltimore School for the Arts, studying poetry, Shakespeare, and Ballet. It was exactly this mix of street struggle and high culture that would go on to make Tupac an iconic figure in both music and fashion.
Just like Biggie, Tupac used contrasting notions and looks to create something wholly original and inspiring. Tupac, after all, was the ‘THUG LIFE’ proponent who put on record that he would kill Biggie’s kids (“My .44 make sho’ all yo kids don’t grow), but who also wrote the tender maternal tribute ‘Dear Mama’. He even said THUG LIFE itself stood for “The Hate U Give Little Infants Fucks Everyone”. A man of extremes in everything he did, including his look.
‘Pac had an impressive output for a man who died at just 25: he recorded 4 albums, starred in 6 films, and left a wealth of unreleased material which is still being revealed to this day. Alongside this creative hoard was an ongoing fashion evolution which, at least at first, he didn’t even acknowledge himself. Kenya Ware, friend to Tupac and stylist, told Complex that Tupac ‘just wanted to stay in the studio and make music. He wasn’t that into fashion straight away’.
It’s quite surprising to hear that he wasn’t into fashion considering he looked completely immersed in style as soon as he burst on to the scene. Just as he seemed to have a natural poeticism he clearly also had a natural style that’s still being imitated to this day: it’s hard to see a pair of dungarees and a knotted bandana without instantly thinking of 2pac.
His relationship with streetwear went right back to his childhood but he would go on to form a close bond with streetwear originator Karl Kani. He did advertising campaigns for Kani for free so as to help take the brand to a wider audience. He was often spotted decked out in Karl Kani, Timberlands, and Carhartt as much as he would be associated with Versace and high-end fashions. Another prime example of his complex and contrasting nature.
Even playing characters in film they would often just be an extension of himself, right down to the look. Often having a say in what his characters would wear most of them dress like Tupac would on any other day such was the impact of his style on his contemporaries as those who would follow.
As a young man who would produce so much in what was essentially just a five year period it’s interesting to see how many looks he would also create, moving from streetwear to haute couture and back again all in such a short time. Lets have a look at some of those styles through the years.
1991 - Juice
It’s odd to see Tupac with hair but we had to include this still from his debut acting role in Juice. His fade and the cut are classic 80s/90s hip hop style along with the Raiders hoodie and blue denim jacket this is a simple but effective look. Whether his idea or the films stylists, he could undoubtedly pull off a style. Also, lets look at that hair one more time, especially as it was about to be gone for good.
Just like that: no hair! You might think of that knotted bandana when you think of ‘Pac but he also favoured a snapback, usually worn in this backwards-to-the-side fashion. Now accessorising with two gold chains and a large Nefertiti pendant, Tupac was beginning to hone his look. Particularly with that amazing Timberland jacket over another favourite: the college or sports jersey.
Only two years in and we’ve got to one of his standard iconic looks: baggy dungarees. Another understated look which somehow comes across as extra. Dark blue Dickies over a long-sleeved, striped, collared tee matched with a thin-striped blue and white oversized cap. The colours work perfectly together to create the illusion of every day wear but in reality, it’s nothing short of beautiful.
Sadly, by 1993, unbeknownst to him, Tupac would already be halfway through his career. It would seem though, this is when he really came into his own. The year that saw the release of his critically acclaimed second album also saw him step up his fashion game another level. Pictured here at the Poetic Justice premiere he’s in full white Karl Kani denim suit, black t-shirt, complete with a gold chain fit for a pharaoh - or for Nefertiti who he would wear just a year prior (and have tattooed on him).
Just one more from 1993 as this one includes his fellow contradictory fashionista Biggie Smalls. Although we can only see the top of his outfit he seems to be channeling his Black Panther heritage with fitted cap reminiscent of the Panthers’ favoured beret and heavy black leather waistcoat. Clearly the rebellious nature is deep within him.
Finally we see the appearance of the iconic bandana, however it’s not quite how it will be remembered: knotted at the front and tied rather than covering the top of the head. Still a perfect example of streetwear meets formal attire as he also wears matching knitted blazer and waistcoat over a light blue paisley shirt. Very much found his stride in this one.
This one isn’t ideal as Tupac is leaving court whilst spitting at reporters but it shows just how much of a change he could go through in a short space of time. He was the sensitive poet who could turn thug rapper in an instant. Also that Detroit Red Wings jersey with matching bandana and light blue baggy jeans is a perfect 90s combo.
At the Soul Train Awards and on the back of a release from prison and the first ever rap double album - All Eyez On Me - ‘Pac came out fighting. In full camo, with black hat, boots, and gloves to match, he seemed to once again be channeling his Black Panther roots at a time when he was vocal about the injustice he felt he had received. Military and inspiring.
With Snoop Dogg at the VMAs in 1996 - the year he would be fatally shot. This time opting for full on formal wear with a couple of little Tupac touches. That garish Versace waistcoat and large chain under a slightly oversized grey suit. All this while throwing up gang signs perfectly encapsulates the complexities of Tupac Shakur and his many facets. He lives on through his music and the person he was.