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The Polo Bear is one of the most diverse and well-travelled graphics within the Ralph Lauren catalog, with the shifting designs ranging from preppy bear, to one fully kitted out in RLX ski gear and our personal favorite, the bear in a tux holding a martini.

Along with the Snow Beach Parka, the Indian Head sweaters remain one of the most covetable Ralph Lauren designs.

Originally a women’s only piece, its loud design—featuring sailing flags, color blocked panels and the regal Ralph Lauren crest—was an early favorite among Lo-Lifes.

As Lo-Lifes and Lo-Heads adopted the designer’s work as their go-to look, wild designs similar to the silk crest shirt were some of the brand’s most popular pieces to purchase, or in some cases, steal from Lauren’s New York City brick-and-mortar stores.

The signature Ralph Lauren Polo bear started as an inside joke among Ralph Lauren employees.

West was a major proponent of the Polo Bear in 2000s hip-hop, but perhaps his greatest homage to the character is seen in the photography for the cover of ; images of West in the “Droput Bear” costume also feature Polo’s bear front and center.

With its extended bill and patched together race entry numbering styles around the crown, it conjures visions of ‘90s sportswear in the way that only excessive decoration can and fortunately, it was re-released this year, marking its 25 year anniversary.

Another piece from the coveted 1992 Stadium Collection, the track-inspired sweater bearing the rarely seen Polo “P Wing” insignia is about as collegiate as they come.

With half a century’s worth of history to its name, the Ralph Lauren brand is one of fashion’s most storied brands.

In an industry populated with European luxury labels, Lauren is one of just a few American labels with the business and prominence to hold its own around the world, with a selection that ranges from the affordable (Polo) to the truly high-end (Purple Label).

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