In 1991, Ralph Lauren introduced the Polo Bear both as a stuffed teddy bear and as a dynamic new icon for a collection of apparel and accessories. The teddy bear, aptly named “Preppy Bear,” was originally produced in a limited run of 200 bears for the Madison Avenue flagship store sold out “in one weekend.”

The bears were produced in collaboration with Richard Steiff’s toy and collectible company. The famous German designer, who passed away in 1939, was one of the original toymakers to develop “teddy” bears in the early 1900s, shortly after The Washington Post ran a cartoon of President Theodore Roosevelt refusing to kill a defenseless bear. Steiff’s bears became the most sought after and valuable bears in the world, eventually finding their way into the hands of Jerry and Ralph Lauren in 1990 as gifts, each bear depicting them in their likenesses. According to the company, the bears wear clothes inspired by, and often made in the same factories as, actual Ralph Lauren clothing.

At the same time, the clothing and accessory lines donning the Polo Bear took off. He could be found on T-shirts, dress shirts, denim jackets and ties. The following year, the Polo Bear sweater would debut, arguably the most popular item of anything featuring the Bear.

The first sweater featured the Polo Bear wearing the famous Ralph Lauren American flag knitted sweater, and it was sold in red or navy. The version sold today is appropriately dubbed the “Iconic Polo Bear Sweater.” It was so successful that it spawned other items later that year, including the James Bond-channeling Martini Bear. There is another crewneck sweater with an “intarsia-knit golfing bear wearing a Fair isle sweater vest, considered by the designers to be the most elaborate bear they ever produced.”

Throughout the ’90s, the Polo Bear would pop up in national print ads wearing everything from a pinstripe suit to a classic Ralph Lauren oxford shirt with a sweater wrapped around his neck. He has been called “the world’s best dressed bear.” The Polo Bear clothing and accessories expanded to bedding, hats, socks and more. They eventually produced a female bear inspired by Naomi Campbell’s look from the Spring 1997 Runway show. Rumor has it there is a “never-ending bear” sweater floating around, where there is a bear wearing a sweater with a bear on it, and so on.

By 2001, Ralph Lauren ended its collaboration with Steiff, and production of Polo Bear apparel ceased as well.

The Polo Bear has taken on a life of his own in pop culture over the last 25 years—specifically in hip-hop—where Ralph Lauren has been embraced for decades, despite it not always being reciprocated. Producer (and famous Polo collector) Just Blaze summed it up best in a 2012 interview with Complex: “Well, it’s aspirational clothing. A lot of his designs were based on things that he wished he had, things that he aspired to, a certain lifestyle he aspired to live. So I think as time progressed into our generation, it’s kind of the same thing. It wasn’t made for us, and hip-hop has always been at its heart about taking things that weren’t necessarily made for us and us appropriating it and making it our own.”

The Polo Bear made somewhat of a comeback in the mid-2000s thanks to Kanye West, who wore a red Bear sweater on the marketing rollout for his debut album College Dropout. West has been seen on more than one occasion wearing Polo Bear apparel during that era, and at a time where throwback jerseys and streetwear labels dominated hip-hop fashion, West carried the flag for Polo and its preppy brand of cool. Everyone from Drake to John Mayer has followed suit, embracing the Polo Bear over the years. Despite a lack of new Polo Bear apparel in production over the ensuing decade, the Bear was more sought after than ever.

One could write an entire book (or produce a documentary) about rap’s embrace of Polo and its lasting influence within the culture. But the fact remains: Kanye West’s obsession with Polo, particularly the Polo Bear, was a seminal moment in the brand’s history.

In 2013, the Polo Bear sweater returned as a part of it’s vintage “Bring it Back” campaign. The Polo Bear picked up where it left off, and in more recent years, while Ralph Lauren’s stock prices slip and sales plummet, the company has decided to lean into its more popular nostalgic collections. Most notably, the ones—like the Polo Bear—which are embraced by a booming streetwear culture.

The limited Snow Beach (or Cold Wave) collection re-release (which is forever immortalized in Wu-Tang Clan’s “Can It Be All So Simple” video thanks to Raekwon) sold out immediately in back January. The same applies to the 1992 Polo Stadium collection, re-released a few months prior. In addition to the traditional Snow Beach clothing, the company re-imagined some of the pieces and swapped out the yellow, red and blue color palette for a more minimalistic black-and-white rendition. Those pieces sold out on their release day as well.

For the Snow Beach release, Polo has, at the very least, acknowledged hip-hop’s influence on the mystique behind this 25 year old collection. RL Mag name-drops Raekwon and hints at the infamous ‘Lo Lifes (the Brooklyn collective who started a Polo craze in late-1980s New York City) when it comes to diagnosing the now-decades-long relevance of Polo apparel. Both are uniquely responsible for Polo Ralph Lauren’s place in hip-hop’s closets even as they were ignored by the company.

Ralph Lauren, like many of his fellow titans of fashion, doesn’t have the best relationship with the hip-hop culture that delivered his company loads of street cred. The Snow Wave drop and subtle Raekwon hat tip are welcome changes to the company’s historical modus operandi. According to Raekwon himself, Ralph still has a ways to go. “You know, Ralph needs to call me anyway and thank me,” he told GQ. “I'm still waiting for him to call me.” Considering it took fellow luxury label Gucci 30 years to properly recognize Dapper Dan’s influence, this is clearly a major break from the once-status quo. Polo’s connection with the street may be unintentional, but it’s definitely part of its 21st century successes.

When Polo Ralph Lauren originally released its Stadium line in 1992, they were never an “official sponsor” of the United States Olympic team, according to The New Yorker. They used the modern American sportsman aesthetic the Olympics represented and jumped at the opportunity to adopt it. Hip-hop has done the same thing over the years. Despite not being intended for them, rappers and those associated with the culture have given Polo—and its charismatic Polo Bear designs—another legacy beyond country clubs and tennis courts, which the company has, and should, capitalize on moving forward.

The Polo Bear category is debatably the most popular—it’s certainly been more available than Polo Stadium or Snow Beach collections, not counting the recent re-releases—offerings of Polo Ralph Lauren clothing within the streetwear community at large. While these retro collections remain limited, at least the reappearance of these classic pieces gave Ralph Lauren much-needed hype for the first time in a while.

This hard switch-up on strategy could benefit a company that has been a bit lost for the past few years. Ralph Lauren recently announced that they will pull a large amount of product from multiple department stores and increase their digital presence. As these re-releases have garnered plenty of brand-driven buzz, Ralph Lauren stands to benefit from the streetwear formula of spaced-out limited drops. Specifically, drops tapping into the Ralph Lauren archive of nostalgic, retro product.

Ralph Lauren has always been a brand that’s drowning in sub-labels (Double RL, Denim & Supply, Polo Ralph Lauren, Lauren Ralph Lauren, Ralph by Ralph Lauren), a reality that has led shoppers to question the core identity that was so central to the brand’s success in the ’90s. Since stepping in as Ralph Lauren CEO, Patrice Louvet has helmed a push towars core pieces and a resurgence of classic styles and symbols as the key to reclaiming the brand’s identity. By pulling out of a slew of department store distributors (approximately 20-25 percent) and reducing overall inventory, Ralph Lauren hopes to connect with customers in a modern way and re-establish itself as a luxury label. Once a symbol of elite tastes and the upper crust American dream, higher off-price sales and an increased presence in outlet stores negatively impacted sales and spurred a decline for the last 11 quarters.

By scaling back and focusing on its core, it has helped the company become profitable again, but it’s still too soon to say if these initiatives will achieve the growth the brand is looking for. Ironically, as divided (and even scattered) as the wider “Ralph Lauren” brand may be, it’s that diversity that has endeared (and literally dressed-up) the Polo Bear since its inception.

Polo Ralph Lauren will always mean polo shirts (still one of the top three best-selling men’s polo shirts in the market), oxfords, peacoats and preppy pieces. Classics stay classics. The real growth, however, may indeed lie in the return of those retro pieces that resonate more with a different subset of the “typical” or “idealized” Ralph Lauren consumer. The Polo Bear stands to be a big part of that movement. Along with being recognizable in the world of streetwear, the Polo Bear has the added benefit of being more mainstream than a Snow Beach collection. You can buy Polo Bear onesies and bedsheets for your kids, while copping a grail-level knit sweater for yourself. Where Snow Beach and Stadium serve as mark-your-calendar releases, the Polo Bear gives consistent sales to a wide range of consumers—something that lies at the very center of the magic of Ralph Lauren; the label may be looking to tighten its offering, but one cannot deny that the appeal of Ralph Lauren is that there’s literally something for every type of shopper. Bloomberg reported earlier this year that “one of the brand’s best sellers of late has been its old Polo Bear sweaters.”

For a brand that’s been a success for many years and means different things to different people, the Polo Bear has proven to be a true symbol for Ralph Lauren’s business. A totem for the various lives and lifestyles that Ralph Lauren outfits, the Polo Bear is a symbol that—unlike any specific collection or runway show—singularly embodies the depth and variety of Ralph Lauren’s designs without betraying the aesthetics and emotions that made Lauren’s brand such a fashion stalwart. The Polo Bear may have been hibernating, but now he’s mounting a comeback. Just like the man who created him.