Two thousand thirteen was on the tail end of the so-called #menswear era. My peers’ obsessions with tailoring, double-monk-strap shoes, and all things prep were coming to an end, but my own fascination wasn’t quite over. The Polo Bear (originally marketed as the “Preppy Bear”) was a grail for me before we used that exact word. I was working in advertising at the time but harbored a desire to write about menswear and woke up hours before I needed to report to my day job to write for tiny sites, pitch stories, and apply for internships. For me, someone still green to the industry, the Polo Bear symbolized everything I wanted to be a part of: a prep icon from America’s most important designer that I had seen over the years on people like Kanye West (still at the peak of his powers then) and John Mayer (stylish, but not yet the Visvim god we know him as today).
But until that night, the Polo Bear was mostly out of reach. The bear was introduced in 1991 after Ralph Lauren employees gave their boss and his brother Jerry teddy bears (made by famous German toy maker Steiff) dressed like them. Lauren was taken with the gift and thought the brand should start selling the plush toys in stores. The first run of 200, dressed in clothes made in the same factory that produced Ralph’s clothes for humans, sold out in a single weekend at the Madison Avenue flagship store.
Ralph Lauren
The bear was so popular the RL team started putting him on everything: sweaters, tees, hats, ties, and denim jackets. The bear (he doesn’t have a name) was like Barbie in his ability to master any profession or skill: in a tuxedo like 007 holding a martini, dressed like a U.S. Olympian toting a basketball, wearing one of Ralph Lauren’s American flag sweaters with his hands tucked in a pair of blue jeans. The bear became a way for Lauren to express the full breadth of his brand, from the ultra-fancy Purple Label to sporty RLX to RRL, which indulged fantasies of storming the western frontier. And I'm far from the only one obsessed with the bears. Lo Lifes, the crew of Ralph Lauren loyalists, prize the furry symbol. "If you're a true collector, having multiple bears in your Polo collection is mandatory," prominent Lo Life Rack-Lo told Fashionista earlier this year. But Polo ceased manufacturing bear-related items in 2001, when Ralph Lauren ended its partnership with Steiff. When did the brand bring the Polo Bear out of hibernation? 2013.
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After a year in Chicago, my girlfriend and I had had enough of the city. It was either bone-chillingly cold or scorching hot. We moved back to the friendlier climate of Southern California. I took an unpaid writing gig for a website, which a couple months later turned into a paid one. Over the years, my Polo Bear sweater allowed me to function in the menswear world even when I didn’t feel like I belonged. When I was assigned to interview a celebrity in person for the first time (RIP, Victor Cruz), I wore the Polo Bear sweater. At the holiday party for my first full-time writing gig, I wore the Polo Bear sweater.
