Black Tuxedo vs. Canadian Tuxedo: Which Matching Outfit With Justin Timberlake Is Crazier? – Readers Poll

The usually fashionable Justin Timberlake raised eyebrows when he showed up to the Sept. 18 premiere of 'Runner Runner' with wife Jessica Biel in matching tuxedos. Unfortunately, this isn't the first time JT has worn a his-and-hers ensemble on the red carpet.

The world remembers all too well the denim outfits he and Britney Spears donned at the 2001 American Music Awards. Which of these matching outfits is more outrageous?

Justin and Jessica are one of the best-dressed couples on the red carpet. Known for taking chances while keeping things classy (Jess did wear a pink wedding dress, after all!), it confused us when they showed up to the premiere in nearly the same outfit! Crisp white shirts, fitted black tux jackets and straight-leg pants -- these two could be twins! We're glad that both of their suits are well-tailored, but we still think it's odd that the couple look nearly identical.

No one will ever be able to forget the Canadian tuxedos Justin and Britney Spears wore way back in 2001. And while the image of the two singers in head-to-toe denim will forever be burned in our minds, let's recap the highlights. Justin's matching cowboy hat, tinted sunglasses and oversize jacked. Brit's strapless gown, coordinating purse and awkward belt. JT and BS may not be together 4eva, but that red carpet look will live on in infamy.

Which of these ladies has the more outrageous matching outfit? Vote in the poll below!