Ralph Lauren Polo Preppy Bear Embroidered Logo

The Story of Ralph Lauren's 'Preppy Bear'

The Origins of the Ralph Lauren Polo Bear

The Ralph Lauren Polo Bear, one of fashion’s most well-known mascots, actually started out as a joke. Jerry Lauren, Ralph’s brother and the company’s creative director, was known to have an extensive collection of Steiff teddy bears in the early 90s. So, as a result of this stitch-up, colleagues decided to give both brothers teddy bears dressed to look like them for their birthdays. The Laurens sensed an opportunity.

The First Polo Bear Collection

The first limited run of 200 Steiff-made, Ralph Lauren-designed bears sold out from the company’s Madison Avenue flagship store in a single weekend. ‘Preppy Bear’, as the teddy was aptly named, quickly returned on t-shirts, dress shirts, denim jackets, and ties before making its debut appearance on the iconic Polo sweater a year later. The bear would go on to pop up in various stylish guises throughout the 90s on both apparel and in print ads, proving to be actions that would only add to the nostalgic pull of garments that the bear appears on today.

The Hiatus and Resurgence of Polo Bear

By 2001, Ralph Lauren had ended its collaboration with Steiff and halted the production of their coveted teddies. Following a resurgence in demand during the mid-2000s for Polo Ralph Lauren items that featured this unique mascot, collectors would search high and wide for highly sought-after vintage pieces that were perhaps the strongest signifiers of the brand's identity in the modern world.

The Return of an Icon

The Polo Bear range finally returned in 2013 as part of Ralph Lauren’s Bring it Back campaign as the brand increasingly focused on its popular nostalgic collections, and ‘Preppy Bear’ has continued to be a fan favourite for a wide number of age groups and demographics ever since. What started as a joke has now translated into unintentionally self-aware clothing, with the bear encompassing the various traits of both the brand itself and its wearers.

The Enduring Appeal of Polo Bear

As the company's creative director was recorded saying, “Who doesn’t love a teddy bear?”.

Frequently Asked Questions About Ralph Lauren’s Preppy Bear Legacy

How did Kanye West shape Preppy Bear’s fame?

In 2004, Kanye West wore a Preppy Bear sweater on his "College Dropout" album cover, sparking hip-hop’s love for Polo Ralph Lauren. His bold styling turned the bear into a streetwear icon, far beyond its preppy roots, influencing its lasting appeal.

What inspired Preppy Bear’s wardrobe variety?

Ralph Lauren’s personal style—think tailored suits and rugby shirts—inspired the bear’s diverse outfits. Designers like Richard Tahsin sketched bears in bespoke guises, from martini-sipping dandies to sporty types, reflecting Lauren’s knack for blending luxury with playfulness.

Why did Preppy Bear join the Lo-Life movement?

The Brooklyn Lo-Life crew, obsessed with Polo’s elite vibe since the 1980s, embraced the Preppy Bear in the 90s. They nicked bear-clad gear to flaunt wealth, making it a gritty symbol of aspiration, distinct from its plush origins.

How rare are vintage Preppy Bear knits?

Pre-2001 Preppy Bear sweaters, like the 1991 RL 92 edition, fetch £500+ at auction due to limited runs. Collectors prize hand-knitted details and faded logos, a stark contrast to the mass-produced 2013 Bring it Back pieces.

What’s the Preppy Bear’s link to Steiff’s craft?

Steiff’s 1902 teddy legacy, born from Theodore Roosevelt’s hunt, shaped the Preppy Bear’s debut. Their mohair expertise gave the 1991 run a plush, durable finish, tying Ralph Lauren’s mascot to a century-old German tradition of quality.

Back to blog