With half a century’s worth of history to its name, the Ralph Lauren brand is one of fashion’s most storied brands. In an industry populated with European luxury labels, Lauren is one of just a few American labels with the business and prominence to hold its own around the world, with a selection that ranges from the affordable (Polo) to the truly high-end (Purple Label). Lauren’s many lines have created a brand that has a unique crossover appeal, and with help from both the Hamptons’ upper crust, and the rebellious Lo-Life Crew of the ‘80s and 90s’—the brand has remained a style stalwart and fashion statement-maker for decades. Throughout its half century in business, the various Ralph Lauren brands have produced a slew of covetable designs, some of which were so popular that they’ve become seasonal inclusions while others have remained relics of past collections and achieved cult-like status. Here, we recount just a few of Ralph Lauren’s greatest grails.

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