Your Ultimate Guide to Mastering Denim on Denim

The denim on denim trend (aka the Canadian Tuxedo) has been around for years now, but maybe you haven't mustered up the courage to try it . . . yet. As much as we appreciate a couple in matching outfits à la Justin Timberlake and Britney Spears at the 2001 AMAs (look how young and in love they were), we're not exactly trying to replicate their look anytime soon.

Truth is, this trend isn't as scary as everyone makes it out to be. Most people give up easily before even trying the look because they don't know where to begin. With a bunch of inspiration (courtesy of these street style shots) and the right items in your closet, mastering a denim on denim look that feels fresh and contemporary is easier than you think. By the end of this, you'll be wondering what took you so long to try this trend in the first place.

We're listing 15 denim-on-denim ensembles to try — along with the best pieces to purchase — that will make you want to give the look another try.