This is why Gregory Porter is wearing the same hat every time you see him

Grammy Award-winning singer-songwriter Gregory Porter has built up a huge following of fans worldwide with his soulful jazz music and unmistakable baritone voice. The 53-year-old has twice won the Grammy Award for best jazz vocal Album, first in 2014 for Liquid Spirit and then again in 2017 for Take Me To The Alley, has just been unveiled as the runner up on 2025’s The Masked Singer UK. After weeks of guesses, it was revealed that Gregory was the man behind the Dressed Crab mask.

His public appearances often leave viewers wondering why he is always seen wearing a flat cap, modified to include a balaclava-style strap that runs under his chin. The same question arose when he performed in the Princess of Wales’ carol service on Christmas Eve last year. He joined fellow singers such as Paloma Faith for the annual Together at Christmas event at Westminster Abbey, also attended by the Prince of Wales and their three children.

So, why does the Sacramento-born musician always wear a hat?. Well, there’s no big mystery – Gregory began wearing the hat, actually a Kangol Summer Spitfire with a modified strap – to cover up scars he has after undergoing skin surgery. ‘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 admitted in 2012 to Jazz Weekly.

Gregory never talks in detail about the scars, though, previously telling the BBC that he wants to be ‘less about my hat and more about my heart and my sound’. ‘People recognise me by it now. It is what it is,’ he added. He did, however, tell the Telegraph in 2016 that he received some facial scars at around ‘seven or eight’ years old but did not elaborate further. Gregory has since opened up about his now-famous headgear to Metro, explaining in a 2020 interview: ‘It started off covering some scars from surgery, but it’s become my style.

‘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.’. He also told us that year that he’s become so synonymous with the hat that he now gets recognised because of it – even when he’s off stage and on holiday.

‘The only time I didn’t get recognised, I took off my hat to swim in the ocean in Ibiza, and no one recognised me,’ he laughed. ‘I went back to my hotel and put my hat on… And there was Gregory Porter. ‘But it’s ok because people are trying to connect and take a picture and say thank you for some joy they had.’. He added on fans asking to take photos with him: ‘I’m really OK with it, and I always honour people, and they honour me by coming to my concerts. I’m thankful.’.

And if you’re wondering whether Gregory has any other hats in his collection, he has assured fans he has several different headpieces to choose from. He also likes wearing a hat and has insisted it never gets itchy, hot, or uncomfortable. Got a story?. If you’ve got a celebrity story, video or pictures get in touch with the Metro.co.uk entertainment team by emailing us celebtips@metro.co.uk, calling 020 3615 2145 or by visiting our Submit Stuff page – we’d love to hear from you.