I recently took the time to pen an essay on Supreme's legacy, the origins of their rise into the mainstream spotlight and what effect that might have on their reputation in the coming years. While I dealt with the broad strokes of what it means for a label of any kind to be "cool," I did not explore the specific garments, items and products that earned Supreme their now legendary status. When ranking the 50 greatest Supreme products of all time, I relished the opportunity to further investigate the idea of what exactly makes Supreme so special.

When evaluating any brand's legacy based on signature pieces we need to use both a micro and macro lens— within the vacuum of the brand itself and its resonance with the outside world. In the case of Supreme this means two things: 1. "How did an item help build Supreme's own reputation?" and 2. "How did an item impact the broader environment of streetwear, fashion and culture in general?" Naturally, the "eye test" also comes into play. Meaning, "Was this shit cool?" because, of course, the "best" pieces are ultimately the ones that we remember most. At the end of the day, ranking anything via superlatives such as "greatest" and "worst" opens the floodgates of subjectivity. No list such as this will ever be entirely satisfactory to everyone. With that said, this list is pretty fucking on point—just something to consider before you take your box logo torches to the comments.

Jake Woolf is a writer living in New York City. You can read his blog here and follow him on Twitter here.