Perhaps Ralph Lauren’s most memorable collection, 1992’s Polo Sport collection took on a life of its own in the early ‘90s and became the object of affection for the Polo-devoted Lo Heads. Worn by Raekwon in the music video for “Can It Be All So Simple,” the Snow Beach Parka typifies the logo-heavy aesthetic that has stormed back in vogue of late and needs no real introduction for anyone that has paid any semblance of attention to the brand in the past 20 years.

The signature Ralph Lauren Polo bear started as an inside joke among Ralph Lauren employees. Inspired by Jerry Lauren’s Steiff teddy bear collection (which according to Ralph Lauren numbers between 30 and 40 bears), company employees gifted both him and Ralph lookalike teddys—Jerry’s in a blue oxford shirt, tartan tie, cable-knit sweater and Ralph’s in Western-inspired gear—for their birthdays in 1990.

From there, a tradition was born. Starting with a limited run of Steiff teddy bears, the bear has become a staple design for the brand and has appeared on a bevy of RL pieces sinces its creation. The bear has adorned many recognizable faces, but it’s hard to top Kanye West when it comes to notable Polo Bear fans. 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 College Dropout; images of West in the “Droput Bear” costume also feature Polo’s bear front and center. 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. Debuting initially as a women’s design for the Polo Country Store in the early ‘90s, the piece found new life in 1994 as a men’s crewneck sweater and has remained a piece that collectors are desperate to track down, and willing to part with the cash to make it happen. While different variations of the indian chief has shown up on assorted pieces over the years, the only real option is the classic emblazoned version with the R.L. 94 below it to show that you went back to the archives to track it down.

This geometric design inspired by the Pueblo and Navajo tribes was a popular print before Ralph Lauren ever discovered it. Beacon Manufacturing company put it on blankets in the ‘30s and the style quickly became a one of the company’s most popular styles. Decades later, it has become a calling card for the Ralph Lauren brand, appearing on sweaters, jackets and throws.

When it comes to 1992’s Stadium Collection, there’s very few pieces that don’t occupy “grail” status. From the windbreaker to the polos, many of the clothes are perennial favorites regardless of your personal polo knowledge. Of course, apparel is the name of the game at Ralph Lauren, but out of the now-classic Stadium Collection, the red hat may be the one stands out most. 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. While Ralph Lauren gear spotted on university grounds is rarely anything beyond the standard Polo shirt bearing the horse logo on the chest, the “P Wing” sweater feels like it was ripped from ‘60s Ivy league track meets and brought into everyday wear. Real Lo Heads will know that, while the American edition features a blue winged foot graphic (as seen on the Stadium Collection reissue), international editions are adorned with a red winged foot graphic. Of all the sweaters released with the P Wing graphic, it is believed that the Red Line iteration is among the rarest and most valuable. Even with the recent reissue, if you still can’t track it down, Noah’s winged foot gear could be a suitable modern day replacement.

The 1994 RL 2000 collection could be seen as a way ahead predecessor to the eventual Polo Sport RLX line that Ralph and company started in 1998 (and would expand and redefine—with a bend towards golf—in the mid-to-late 2000s). The white skier that adorns the back of the jacket helped the piece earn its nickname, but as Lo heads and collectors looked back on Lauren’s design archive, the “ghost” nickname took on a new meaning; after 1994’s RL 2000 series, the brand slowly began to phase out its more ostentatious designs in favor of more “classically American” aesthetics. The performance-focused, technical gear was out of character for Ralph’s aesthetic at the time, but the collection and most notably this jacket, is looked back upon fondly.

In the outerwear discussion, few pieces can eclipse the history and look of the classic camel hair Polo coat. A Ralph Lauren ad campaign regular, the original camel hair coat design has roots as outerwear for British officers in colonial India. That said, its name as the "polo coat" means far more than its relationship to the Ralph Lauren label. A favorite among polo players as a casual outer layer to be worn in between chukkers (or periods), the coat was sported by players both during and after matches, eventually making its way into the stands as polo spectators became enamored with the look. The polo coat quickly became popular among the Ivy League crowd, ultimately becoming a general menswear favorite thanks to camel hair's lightweight, but weather insulating, qualities.

All that said, one look at its silhouette however, and its combination of both formality and simple comfort, have made it a favorite among men and women across decades. Its details on their own don’t stand out much, but all used together on a single coat, they create a piece greater than the sum of the parts. Enormous peak lapels on a double breasted cut combine with the half-belt detailing at the rear and flap pockets throughout to create a relic of the past that oozes brilliance in today’s dress code.

The silk crest shirt represents a significant phase in Ralph Lauren’s history. 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. Ralph may not have known how to welcome or embrace the community to save his life, but the fans and followers continued to stock up on the bolder, brighter pieces and have given them a reputation that lives on to this day.

This one needs little to no explanation. The quintessential American clothing brand turned the quintessential American symbol into a quintessential piece of American clothing. Its key detail is the inclusion of 13, not 50, stars on the US Flag graphic. According to Ralph Lauren, its a nod to the flag “that flew over Fort McHenry during the War of 1812, which inspired Francis Scott Key to write "The Star-Spangled Banner," and the restoration of which Ralph Lauren generously helped underwrite in 1998.” They’ve done it many times over the years and every season, it remains a standout. Given how essential Ralph has been to American design for decades, it makes sense that he’d have a patriotic side as well.