Shaggy shows off signature style and philanthropy during NBC TODAY ‘Girls Trip’ in Jamaica

Grammy-winning hitmaker Shaggy proved why he remains one of Jamaica’s most enduring style icons when he appeared on NBC’s TODAY Show with hosts Jenna Bush Hager and Sheinelle Jones during their special “girls trip” to Sandals Dunn’s River.

The “It Wasn’t Me” DJ, who recently found himself at the center of a viral fashion conversation, did not shy away from the topic. Instead, he did what seasoned entertainers do best — leaned into it.

“I’ve always been about expression,” Shaggy shared with Jenna and Sheinelle during the NBC interview, declaring, “Style is just another way to show who you are, no boundaries.”

He said he reposted memes, including one featuring his dog wearing his now-famous outfit, telling viewers, “There’s always going to be opinions, but confidence? That’s the real style.”

At Sandals, dressed in a brown fitted, short-sleeve crewneck T-shirt tailored to show off his physique, along with his now-famous pearl necklace and trademark confidence, Shaggy added, “Music is about freedom, and so is fashion,” adding, “If you feel good in it, wear it. Simple as that.”

Shaggy also promoted his new single, “Looking Lovely,” featuring American R&B star Robin Thicke. He also spoke about his philanthropic initiative for hospitals in Jamaica following Hurricane Melissa, discussing his dedication to raising funds for Bustamante Hospital for Children in Kingston and highlighting the importance of giving back to his country.

Also making an appearance was Jamaican-American actress Sheryl Lee Ralph, who spoke about her Jamaican pride and self-love, emphasizing the importance of staying true to oneself.

“Keep showing up. Keep being your authentic self. Keep speaking the truth,” she shared.

Jenna and Sheinelle also leaned into a culinary feature with Chef Andre Fowler, who brought local Jamaican flavors to the Sandals resort. While in Jamaica, the NBC hosts also experienced bobsledding at Mystic Mountain, visited Dunn’s River Falls, went tubing in Ocho Rios, and dined at the popular Miss T’s Kitchen.

The “girls trip” to Jamaica was held in collaboration with the Jamaica Tourist Board and Sandals Dunn’s River, with the aim of showcasing the culture and beauty of the island. A lucky TV viewer and a guest also won a free trip for the live broadcast in Ocho Rios.