The 1992 ‘Sit Down Bear’ Polo Sweater is a rare piece that perfectly captures the intersection of Polo Ralph Lauren’s preppy aesthetic and hip-hop’s constantly evolving style. Kanye West, known for blending high-end fashion with streetwear, frequently wore it in the early 2000s, bringing a new appreciation for it to a younger audience. As he redefined hip-hop fashion, this sweater became a key part of his signature look, influencing a new wave of style-conscious rap fans. Today, it remains a classic among collector’s, symbolizing both deep hip-hop roots and Kanye’s early impact on fashion.

Measurements: Pit to pit: 24 inches (approximately)

Top to bottom: 26 inches (approximately)