While most guys are dressing for Memorial Day weekend in basic polos and chinos (maybe a pair of Nantucket red shorts if they’re feeling festive) there are a few brave men who cannonball into summer style without a care in the world for how crazy they look. Usher did just that yesterday in Las Vegas, donning a Hawaiian shirt with matching pink aviators and pool slides to a party at Rehab. It’s an outfit that feels a little bit like an ode to Fear and Loathing in Las Vegas or Spring Breakers, walking the line between stylish and completely insane.
It helps that all of the elements in Usher’s look are relevant in menswear right now, and therefore don’t feel completely out of left field. In fact, we could see the music veteran wearing these items individually under slightly soberer circumstances in the warm weeks to come. The slouchy utility shorts would look great with a hoodie and sneakers for errand-running in LA, for example. The layered necklaces, meanwhile, are begging to be worn on stage with a vintage T-shirt, jeans, and suede boots. And those sunglasses with a slim suit for a late-night appearance? Strong move. In fact, Usher could probably have his most stylish summer ever just by riffing on the different elements in this look.
And that right there is the benefit of going for it with your clothes right out of the gate. You’ve set the style bar high (and crazy) for yourself early on, ensuring that when summer laziness hits, you won’t just reach for the boring stuff over and over again.