Gregory began wearing the hat, a Kangol Summer Spitfire with a modified strap, to conceal the scars he received after skin surgery.
In 2012, he acknowledged to Jazz Weekly, "I've had some surgery on my skin, so this has been my look for a little time and will continue to be for a while longer."
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Although he never discusses the scars in detail, telling the BBC that he wants to be known for his heart and sound rather than his hat, he added: 'People recognize me by it today.' 'It is what it is,' says Gregory.
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