8. Illegal Business Controls America, 2003/2007

In 2003, Supreme released a photo-print tee depicting financial broker Igor Kotlyar in handcuffs following his conviction for fraud. In the photo, Igor wears a Supreme box logo T-shirt—a prime example of Supreme's ability to capitalize on a PR moment thanks to sheer luck. The subsequent photo tee, "Illegal Business Controls America," came out late that year and that theme was capitalized (no pun intended) on once more, this time in hoodie form, 4 years later. At the time, all-over print hoodies were going strong thanks to Bape. Supreme's subversive wink at the trend was a stroke of genius.