Ever since Tyler, The Creator rocked that heather grey Supreme box logo hoodie for his first live TV performance on Late Night with Jimmy Fallon, his reputation as a style icon has been crystallized. 

Compared to his rap peers, Tyler was never one to dress himself in crazy amounts of high end designer labels. Instead, Tyler has mostly stayed true to his roots as a skate rat who grew up around Fairfax. To this day, all Tyler really needs is a pair of skate shoes, a hat, a T-shirt, and a hoodie. If he ever turns the drip knob up, it usually consists of clothing that he’s made for his own brand, Golf Wang. But in recent years, he’s also developed a taste for more sartorial styles. Nowadays, he’s seen wearing tailored suits, loafers, calm knits, and other dapper fits. 

To celebrate the release of his latest album, Call Me If You Get Lost, we gathered some of the rapper’s greatest fits over the years. Take a look at how Tyler, the Creator’s fits have changed since his chaotic days of the Odd Future era to the avant-garde looks he wore throughout his Igor phase.