The album's cover was handled by art director Eric Duvauchelle of Roc-A-Fella Records, which depicts the Dropout bear in a school gymnasium, wearing a suit coat, red t-shirt, and jeans.

The mascot has goggle eyes, perky ears, and a collegian outfit, wearing a blazer with a school insignia.

In the album booklet, Dropout Bear appears in the university, sitting alone in classrooms and reads books before exiting.

Often called "the Warhol of Japan", Murakami's surrealistic visual art is characterized by cartoonish creatures that appear friendly and cheerful at first glance, but possess dark, twisted undertones.

Takashi Murakami had stated that West had brought forward the idea of portraying an anthropomorphized bear and fox, to reflect him and Cudi, respectively.