Sometimes it's about who wore him better, and other times it's about who wore him worse... this might be "other times."
Justin Timberlake has settled down with Jessica Biel, but before that happened - there were a lot of young stars and memorable fashion mistakes. Shall we take a little trip down memory lane?
Surely you remember his days with Britney Spears, but did you know that first he dated Fergie?? This is so long ago that back then, she was still known as Stacy Ferguson! This might be one of the craziest relationships buried in Hollywood history. Justin was only 16 years old and Fergie was 23. This picture was taken years after they split, making these weird sort of pilgrim-looking outfits even more confusing. What should I wear to see my ex today? I know, I'll dress up like Heidi!
Britney - we see you laughing, and we're laughing too. Not just with you, but also at you for this 90s-fabulous ensemble. The light pink slip thingy, boots and matching hat are pretty hilarious, but not as hilarious as Justin's... um... leather chaps?! We're not entirely sure what we're looking at here. These two definitely came up with some entertaining outfits in their years together.
These outfits are both so horrible and the relationships are ancient history. We're going to give this one to Britney though. Thanks - as always - for the entertainment, Brit!