2000, Jennifer Lopez and P-Diddy

When it comes to leaving a lasting impression with her fashion choices, Jennifer Lopez is a true master. While her iconic green dress from the 2000 Grammy Awards remains etched in our memory, another unforgettable moment took place that same year at the MTV VMAs, and it wasn’t just about her.

At the VMAs, J.Lo made a style statement that was as memorable as it was iconic, coordinating her outfit with her then-boyfriend, Sean Combs. She proudly sported her ex-beau’s label, bedazzling Sean John across her shirt (who can forget Sean John clothing?) and adding a matching bandana to complete the look.