Grailed x Polo Sport launches Thursday, May 30th, at 12PM EST. Preview the entire drop here.

When it comes to crafting a family of fashion lines, none have mastered the art better than Ralph Lauren. With a wide array of brands that compose and define a single, signature “lifestyle,” Lauren has created iconic brands that can appeal to anyone at virtually any style or taste—without sacrificing the core values and aesthetics that make Ralph Lauren, “Ralph Lauren.”

A classic example is Polo Sport. Created as an offshoot to Lauren’s larger collections, Polo Sport began as literal nods to sportswear within the main line, evolving into a label that became a streetwear and pop culture stalwart the 1990s and early-2000s. With such a decades-spanning reach, it can be hard to pin down the best of the best when it comes to Polo Sport. While it would be nearly impossible to chart out the expansive influence of the brand, we want to shine a light on a few key pieces that truly embody the best of what Polo Sport was—and still is—today.

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