When iconic fashion moments of South African history come to mind, it is an unspeakable sin not to mention the unforgettable ponytail rapper Cassper Nyovest whipped onto our screens following the success of his debut single, Doc Shebeleza.

While his music, beefs, and catchphrases have earned him notoriety over the years, Cassper has proven to be a formidable force on and off the mic.

Whether you know him as Mr Fill Up or the Fresh Prince of Maftown, here is a look at Mufasa’s glow up and style evolution.

The fresh prince of ponytails (2013)

When Cassper first stepped into the scene, he was already a formidable name in the rap game. He had been hosting The Fresh Prince of Maftown event since 2010.

While his music was the perfect blend of kwaito-meets-hip-hop, so was his style, comprising of basketball jerseys, shorts and tube socks, which he often paired with African-print baseball caps, colourful sweaters, and gaudy shirts.

Cassper has never been one to blend into the background, so naturally his ponytail added a fashion-forward mix to an already unique style.

Hip-hop Nyovest (2014)

By the time his chart-topping self-titled debut album Tsholofelo rolled out, Cassper had a more succinct interpretation of his hip-hop flair.

With bold colours, bucket hats, and the signature kasi-boy neck pieces, Cassper seemed to harken his style from Hip Hop Pantsula, who was a major influence in his early career.

Building the brand (2015)

Racking up award nominations and more fans, Cassper had begun spending more time on stage and in the spotlight.

Releasing his sophomore album that same year, Refiloe, Cassper stayed true to his casual nature with the release of his branded caps, tees and even crop tops. He also proved to be quite the bankable artist by fulfilling his #FillUp mission at The Coca-Cola Dome.

Still stuck in his ways in terms of monochromatic fashion, Cassper played with more textures when taking ventures outside of the world of football and basketball jerseys. Take this all-white ensemble from the African Hip Hop Awards.

The "Fill Up" dzaddy (2016)

Hip-hop heavyweights Big Sean, Rick Ross and Drake are among many rappers who have elevated expectations of sophisticated glamour for hip-hop stars on red carpets.

While Cassper traditionally followed existing trends in streetwear, Mr Fill Up slimmed down in the run-up to the sequel, set to take place at the Orlando Stadium in Soweto. With a smaller frame and bigger ambitions, Cassper was on the tail of the trending male-cleavage style.

His understated use of gold chains was taken up a notch with the inclusion of more watches and rings. This would open avenues to a much sexier style for Cassper.

Glow up Nyovest (2017)

With fellow artists like Riky Rick earning points as style icons, Cassper began shedding an all-new fashion skin.

While he was cleaning out at award shows, he had also cleaned up his look as a more polished rapper.

While he had not completely abandoned his tube socks and bucket hats, he traded them for silky cravats and form-fitting suits on red carpets and at events.

Guns out for the Gram (2018)

Cassper’s body transformation hit a pinnacle in 2018, when you could not turn on the TV or log onto social media without seeing the rapper celebrating his transformation.

The rapper had come full circle, embracing his hip-hop flair and kasi style with a sexier remix including wearing fewer items than usual. When he wasn’t sporting darker tones, Cassper opted for colour-blocked combinations, making him a major player in the world of athleisure.

That year he was also a part of Ciroc’s collaboration with American fashion house Moschino, along with fellow South African personality, Thando Thabethe. Cassper also collaborated with singer Jason Derulo on the Fifa World Cup theme song.

Bling it on (2019-2020)

While it has become standard that Cassper will sell out venues, win many awards and bag endorsement deal after endorsement deal, there have been a few new avenues to take in his style journey.

His slouchy, comfortable style made a luxe comeback with the inclusion of the daring prints and colours he’s always been known for.

Adding on to his signature excessive style, Cassper has added bolder neck pieces, eye-catching rings and watches, with muted eyewear to balance things out.