Wearing denim-on-denim has been frowned upon since that unforgettable moment when then-couple Justin Timberlake and Britney Spears showed up at the 2001 American Music Awards wearing matching Canadian tuxedos. Pairing a denim jacket with jeans was popular on designer runways and amongst boy bands like N'Sync in the '90s, and until now, we were happy to let that trend remain in the past.
Lately though, the style has resurfaced, thanks in large part to Jenna Lyons and her way with chambray. The J.Crew president and creative director was spotted in 2010 wearing one of the brand's signature button-downs in the light fabric, paired with cropped jeans and super sexy Louboutins. We saw bloggers like Leandra Medine of the Man Repeller replicating the look, and from there, the trend spread like wildfire. Recently, we've seen the newly-single Katie Holmes out and about in a Canadian tux, and looking quite adorable.
But how is it OK that a trend that was deemed laughable in the '90s is back with a vengeance? Well, that's the way trends work: They go out of fashion, only to be reimagined and tweaked, and, like a phoenix, they rise from the ashes.
The key to wearing this updated pairing is simple: Make sure the two items aren't the same color. They can both be blue jeans, but the shade has to be different, or you will be pointed out as a "fashion don't." Our favorite iteration on the trend is a light blue chambray shirt with dark blue boyfriend jeans, just like Jenna did. The look also transitions easily: Wear with leather sandals and a neon cross-body bag during the day, and add heels, a sleek clutch and a bit of sparkle for a night out.
Here 44 celebrities wearing denim-on-denim (some got it right, and some got it so wrong), plus a few shoppable options in case you'd like to try it for yourself.