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I see celebrities killing it with the black-suit/white-shirt/solid-black-tie look. But when I try it, it's like I'm either going to a funeral or in the casket myself. What am I getting wrong?
Pulling off a black suit is like making perfect scrambled eggs. It's so damn simple and so essential—and so easy to botch. I blame Hollywood. Movies like The Matrix use black suits as a generic Institutional Drone signifier. It's as if you put one on and instantly become enigmatic. But if you zoom in, those suits are as ill-fitting as they are evil, with tie bars longer than their ties and sunglasses from a QuikTrip. So the first rule is: Always draw your black-suit inspiration from musicians and artists. Because they're not acting cool. They actually are.
Look beyond the Rat Pack to Kanye's early-2010s Rosewood era. Ye and his crew knew that the key to the classic combo is keeping the proportions consistent. Slim fit, slim lapel, skinny tie, small collar, etc. Or go big like Tom Ford (speaking of artists): wide peak lapel, full pants, big collar, even bigger ego.
But there's something even the perfect fit can't impart: mojo. Everyone (including me) credits jazz musicians like Miles Davis and Thelonious Monk when they talk about looking sharp in a suit, but most of them were pretty broke and toured around in cheap polyester they were able to have cleaned or replaced very easily. What made them gods of cool suiting is that they knew wearing a suit is a badass privilege. There's not a shot of Charles Mingus dressed in black where he looks anything but proud—of his talent and his clothes. So find yourself a suit, make sure it fits, and then act like a man who deserves to wear it.
If you can spend some coin, go to Dior and buy the staple slim black two-piece. It's the (black) gold standard. Legend has it that Karl Lagerfeld lost 50 pounds in the 2000s just so he could fit into one. (I bet they have your size.) While you're there, pick up the shirt and tie, too. Sure, it won't be cheap. But at least you'll save on gas by shopping at one place.
