While Polo Sport had made its name by plastering its two word logo over a myriad of different garments during its run, this piece is unique for being an alteration on the familiar wordmark. Released in 1999, the alternate logo was Polo’s nod to the incoming new millennium. As items with this branding were released in such a short time span, they’re a surprisingly unique, rare take on Polo Sport.

A full-zip cycling jacket that originally debuted in Fall 1997, this piece of outerwear is significant for its unique rework of the Polo Sport logo, earning its nickname thanks to its resemblance (in both the typeface and the color scheme) to the Pepsi logo of the 1990s. Accented with a back zip pouch pocket, even Lo Heads consider it a true Polo Sport grail.

Given that the history of the Polo Bear is nearly as old and storied as the Ralph Lauren label itself, it’s not an easy task to select our favorite iteration on the world’s most stylish bear. However, while Polo Sport does play host to the ever-popular “Basketball Bear,” it’s the “Motorcycle Bear” that only Polo Sport could create. Featuring the signature bear sporting a quilted, yellow, Polo Sport-branded biking jacket (with a cycling cap to match), it’s a surprisingly badass iteration of the Polo Bear.

Ralph Lauren, and especially Polo Sport, has used its collections to highlight and take inspiration from various athletic activities over the years. While some may quickly think of golf, rugby or skiing, this piece is unique for its use of motorcross. Released for Fall 2000 season and hailing from the “Ridgway” Polo Sport collection, the garments in this particular collection took cues from dirtbikes and motocross, as well as bull riding and rodeo culture. With the longsleeve tee’s unique all-over graphic, it’s easy to spot the Polo Sport branding, seen clearly on the biker’s goggles and pants.

Polo Country stands apart in the wider graphic library of Ralph Lauren. A nod to the traditional American hunting and fishing magazines of the 1940s and 50s, Polo Country (and Polo Sportsman) were one of Lauren’s many nods to the hallmarks of American life. Seen here on the Hudson Jacket, this anorak—originally released as a part of Spring 1996’s “American Sportsman” collection—stands apart from its Polo Sport brethren for its relative lack of branding, save for the mountain Polo Sport "cookie" patch affixed to the left sleeve.

While brands like Supreme have proliferated and popularized the sling, shoulder and waist bags in the present day, it’s refreshing to see they’re not the ones who helped bring the accessory into sport and streetwear scenes. Released for the Spring 1995 season, the bag is notable for being featured prominently around the waist of the brand’s signature model—Tyson Beckford—in a Polo Sport ad from the same year.