While some of the die-hard watch nerds reading this might be thinking "Wait, why are we reading about teddy bear watches on HODINKEE?," I beg you to stick with me on this one. The Polo Bear has real history and is something worth knowing about. It dates back to 1991, when Ralph Lauren employees supposedly bought both Ralph and his brother Jerry Lauren teddy bears as gifts – only the bears were dressed up like their bosses. The two men were charmed and thought it would be fun to sell a limited run of the bears at the Ralph Lauren Mansion on Madison Avenue. They sold out quickly, and then the Polo Bear started making its way onto everything from sweaters, sweatshirts, and other Ralph Lauren goods. Now, nearly 29 years later, there are collectors dedicated to just Polo Bear merch, hunting Ebay, flea markets, and estate sales for rare variations. (You don't have to take my word for it either.) Sometimes the Polo Bear is surfing, and sometimes he's relaxing, but he's always decked out in head-to-toe Ralph Lauren. It's a perfect example of Ralph Lauren's ethos of doing serious things without taking himself too seriously.