Justin Timberlake Does Know How to Wear Head-to-Toe Denim

Forever topping the list of iconically bad celebrity outfits is Justin Timberlake and Britney Spears’ matching head-to-toe denim looks (or lewks in this case?) from the American Music Awards way back in 2001. Like the infamous ramen noodle hair that defined much of his NSYNC days, Timberlake’s clothing choices–especially that denim fit–refuse to ride off into the sartorial sunset. In fact, it was the first (only?) thing we could think of when we spotted him last night at Dodger Stadium in a far (far, far, faaaaaaar) superior double denim outfit.

Where there was once a blazer and stacked patch-worked bootcut jeans (and, don’t forget, a matching cowboy hat), there are now light wash jeans with subtle rips at the knees and a short sleeve denim overshirt. It was the opposite of overkill. It was simple. It was effective. It was the right balance of denim layered together (with a white tee and clean white sneakers, no less). It was cool.

Timberlake’s dad years are turning out to be his most experimentally stylish–which is a good thing. Where most regular dudes hit their fashion peak and then don’t have the time to focus on it in the face of fatherhood (babies > clothes), Timberlake has accomplished the reverse. His world series casual fit isn’t completely free of boy band vibes (you can take the man out of the 90s but you can never take the 90s out of the man), but with this combination Timberlake found a grown up way to translate his personal brand. The fit of his jeans is slim but not skinny, the wash is light without being acid washed or aggressively distressed, and his denim shirt is showing off his sculpted arms without looking cheesy.

It’s a smart move for guys who aren’t just world-famous entertainers like Justin Timberlake. Everyone can and should think about upgrading some of their less than successful past outfits. You’d be surprised what a little self reflection can do for your wardrobe.

GQ