Britney Spears and Justin Timberlake

We all remember the time pop icons Britney Spears and Justin Timberlake were a couple. Back in the late 90s, when the two went public with their relationship, they weren’t just pop stars, but fashion icons as well. They were the ones who made denim on denim a thing when they showed up on the red carpet wearing full denim suits.

At the time, they were probably pretty happy about their trendsetting look, but looking back at those days, over two decades later, it’s safe to say it’s a look both of them would like to forget. The two split up in 2002 in a messy breakup, but unfortunately for them, those images of the denim outfits would always be on the web to haunt them.