You've probably seen the photos of JT and Britney Spears decked out in matching denim outfits for the American Music Awards Show in 2001. It's a classic example of a fun idea that just didn't work. All that stonewashed blue looks juvenile and a bit silly today. In a recent Playboy article, JT even admitted the choice was cringe worthy. If your best gal pal thinks matching Ts or (horrors!) Christmas sweaters are a great idea, nix the notion fast and make it final.