Gregory Porter; The Story Behind the Iconic Hat and His Journey Through Music and Loss

2025-03-02

Grammy Award-winning jazz singer Gregory Porter has revealed the poignant reason behind his signature black deerstalker hat, which has become an iconic part of his stage presence. The 53-year-old musician, known for his soulful voice and twice-winning the Grammy for Best Jazz Vocal Album, explained that the hat initially served to cover facial scars resulting from surgery he underwent as a child. In a 2012 interview with Jazz Weekly, Porter shared, “I’ve had some surgery on my skin, so this has been my look for a little while and will continue to be for a while longer.” He later told The Telegraph in 2016 that he acquired the scars around the age of seven or eight but did not elaborate further.

Porter also recounted how the hat became a permanent part of his style during a cold stint in Denver. “It started off covering some scars from surgery, but it’s become my style,” he told Metro in 2020. “I was in Denver, and it was cold. I was wearing five layers of clothing, and I wore a hat. It warmed up, and I thought, ‘Actually, this is comfortable; this is a look.’ I started to sing in a jazz club in Denver, and people were like, ‘Oh yeah, that’s the guy with the hat.’ So it became a thing.”

In addition to his distinctive fashion choice, Porter has faced profound personal losses. His brother, Lloyd Cornelius Porter, tragically passed away in May 2020 due to complications from COVID-19. Gregory sang to his brother as he lay intubated in hospital, a moment he described as heartbreaking. “I sang to him. But at the opportunity that I sang to him, I said, ‘He’s gone,’” he told The Irish Times. “He was intubated. He was in that early [wave] that came through New York. They were super careful. They were burning the bodies or freezing them. He disappeared. He went in, intubated that day – and he just disappeared.”

Porter also reflected on the loss of his mother when he was just 21. She encouraged him to pursue music, a passion he has carried forward throughout his career. “She said to me… two days before she passed, she said, ‘Gregory, music is the best thing you do. Don’t forget about your music,’” he recalled.

Gregory Porter is married to Victoria, a Russian painter, and the couple have two sons. The family resides in Bakersfield, California, where Porter continues to balance his music career with family life. He has also taken up learning Russian, his wife’s native language, alongside his son. “It’s fun, working on my wife’s native language — and I guess it’s half of my son’s language as well, because he goes to Russia every summer,” he said.

In a recent turn of events, Porter was unmasked as Dressed Crab on The Masked Singer UK in 2025, finishing in second place behind Pufferfish, revealed to be Samantha Barks. Fans had long speculated that the Dressed Crab character was Porter, given his distinctive voice and style. The show’s finale saw Porter, alongside Wolf (unmasked as Marti Pellow) and Pufferfish, battle it out in an extended episode, cementing his status as a beloved figure in both music and popular culture.

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