Bennett 's fashion style is a large part of his public image , and he has taken interest in the industry . Bennett has designed hats for the Chicago White Sox . '' The Hollywood Reporter '' has said that Bennett is " redefining fashion " with his style of generally wearing overalls and contesting traditional hip-hop fashion norms . Bennett wore a suit that was meant to imitate Michael Jackson at the 2017 BET Awards . Bennett was seen wearing Thom Browne clothing at the 2017 Grammys . Bennett has been known to wear a signature hat with the number three on it . “ I ’ve rationalized it to myself that it stands for the third mixtape , the Holy Trinity , and the three-pronged family of myself , my daughter , and my girl . ” Bennett said in an interview in regards to the meaning of the number three
2017 Grammys
59th Annual Grammy Awards
Chance the Rapper