Karl Kani vest, cotton and wool, 1990s, USA, gift of Antonio Gray

Brooklyn-born Karl Kani was one of the first streetwear designers and is known as “the godfather of hip hop fashion.” He established his brand in 1989, pioneering the baggy jean look. His designs were favored by hip hop artists including Biggie Smalls—who named dropped Kani in “One more Chance” (1994)—Nas, Jay-Z, and Tupac Shakur who famously appeared in Karl Kani ads for free because of his support for the brand. Shakur wore this plaid vest style in the 1990s illustrating Kani’s sophisticated blend of classic fabrics, workwear inspiration, and oversized silhouettes.