The story of the Polo Bear begins not in 1991, when he first made a debut, but in 1902, when President Theodore Roosevelt went on a bear hunt in Mississippi. When Roosevelt declined to shoot a bear tied to a tree after a failed hunt, The Washington Post ran a cartoon of the event, inspiring toy sellers to name stuffed bears after him. Richard Steiff, one of the world’s most renowned toymakers, was amongst them.

As chance would have it, Jerry Lauren, Ralph Lauren’s brother, is a passionate collector of Steiff bears. In 1990, Jerry’s colleagues had a Steiff bear dressed in Jerry’s likeness—blue oxford shirt, tartan tie, cable-knit sweater—and presented it to him for his birthday. At the same time, a Western-inspired bear was given to Ralph.

As with so much in the World of Ralph Lauren, what appealed to Ralph in his own life made its way to the clothes, and in 1991 the Polo Bear appeared in two very different forms. The first was an actual teddy bear (“Preppy Bear”), produced in tandem with Steiff. Massively popular, the limited run of 200 sold out in one weekend at the Madison Avenue flagship. The second iteration appeared as a graphic on everything from T-shirts and denim jackets to dress shirts and ties.

The next year, a Polo Bear wearing an American flag sweater was hand-knit onto a Polo Ralph Lauren sweater, and over the next several years, the Polo Bear appeared in a series of national ad campaigns. From Martini Bear to Safari Bear and a Purple Label debut to the app fan-favorite Collegiate Bear and the Polo Bear watch collection, created in celebration of Ralph Lauren’s 50th anniversary, the iconic character has remained a mainstay of the brand through the decades.