People recognize me by it now. Eventually, it became synonymous with his work as an artist, and … It is what it … Porter replied: "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. If you are an adherent follower of Gregory Porter then you will notice that over the years, you have never seen a picture of him without his hat on. Why Does He Always Wear Hats. Why Does Gregory Porter Wear a Hat? Following an operation, Gregory decided to cover up the procedure by wearing a hat. Asked in Clothing Why does Gregory Porter wear a hat? There is no mention of his neck found but he does wear a modified flat cap. A balaclava is a ski mask, so you wear it on your head. Gregory Porter started wearing a hat due to a skin condition on his face and neck area. Asked in English to French Gregory Porter – I Wonder Who My Daddy Is (Live At The Royal Albert Hall / 02 April 2018) Because he is making a bizarre style statement, and he is a daft herbert. The jazz vocalist Gregory Porter was born in November 1971 in Los Angeles.