“Me treat artist business like a athlete”: Shaggy Opens Up About Fashion, Fitness and Focus

According to Shaggy, his relationship with Versace placed him directly inside one of fashion’s most elite circles.

In an exclusive World Music Views sit down, the Jamaican superstar opened up about a lesser-known chapter of his career: his deep connections with some of the world’s most iconic fashion houses during the height of his 1990s success.

He recently created a viral TV fashion moment on the Sherrie Shepherd Show, but incorporating high fashion in his promotions and brand is nothing new for the Lucky Day singer. Shaggy’s “Boombastic” became a global anthem and gained massive international exposure after being featured in a Levi’s clay-mation commercial and he says during the period he was walking all the fashion week shows for top brands.

“In the earlier days, like in Boombastic Time, too, I was at a lot of those shows… like me and Gianni Versace was really, really a friend,” he says. Adding, “I had, on all of his runways, I used to be, on the front row of that on multiple of them,” he says.

After Versace’s passing, Shaggy continued building relationships across the fashion world, working with other legendary brands such as Dolce & Gabbana and Giorgio Armani.

“And then Dolce & Gabbana after a while… I ended up doing… it’s a bunch of fashion houses. Armani too… I did his show also,” he says.

“I used to do tons of those… just bunch of free clothes and come and made sure I was on every runway show at that time in Italy.”

Despite being surrounded by opportunity, Shaggy admits that he and his team didn’t fully grasp the long-term branding potential of those moments.

“Even though we were thrust in the middle of it, we just didn’t have the people around us that really understood it… what the value of the brand was… so it passed us.”

Still, he believes the connection between artists and fashion is stronger than ever—and that today’s generation is better positioned to capitalize on it.

“They could be, it’s their time, really… I’ve been following Fashion Week… New York Fashion Week… Paris, Milan… I could see you walking the red carpet, or even online.”

Beyond fashion, Shaggy also addressed one of the most talked-about aspects of his public image—his youthful appearance. When asked about the secret behind it, his answer was simple and disciplined.

“Well, you just come right and say, it’s in my gym. I’m in that every single morning… with a trainer every morning.”

For Shaggy, maintaining his physical condition is no different from maintaining his career.

“Me treat artist business like a athlete.”

Shaggy released the tracklist for his 17th studio album Lottery out May 15, 2026 featuring Vanessa Amorosi, Mutabaruka, Jeremih, Akon, Aidonia, Robin Thicke, Beres Hammond, Dexta Daps, Sting, 450, Anthony Hamilton, Noah Powa, Olaf Blackwood and Rayvon.