Men’s Style Madness 2017 Sweet Sixteen: Kennedy & Basquiat

Men’s Style Madness 2017 Sweet Sixteen: Kennedy & Basquiat

Past Performers and Dark Horse Newcomer

By Gabi Meyers | Last Updated: Jan 30 2019 | 2 min read

Welcome to the Madness! Voting is simple – pick the most stylish guy by clicking on their name in the match up – no login required. Feel free to share your bracket with us and sway a few votes in the comments below. So, who ya got?

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Jeff Goldblum vs. DeAndre Hopkins

Jeff Goldblum

Jeff Goldblum’s style is playful and put together. He’s in his sixties and pulls off skinny jeans. He rocks pattern on pattern. He has honed the power of accessories, whether it be his signature thick-rimmed glasses, a fedora, or a skinny tie. If this man can make a zebra print polo look cool, what can’t he do?

DeAndre Hopkins


DeAndre Hopkins can make even a hoodie look polished. His style statements run both big and small, whether it be a fun sock in an otherwise basic outfit or a totally tricked out formalwear look. His hair is definitely a style that most guys couldn’t imagine pulling off, but his confidence (and cheekbones) make it look like a breeze.

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Eddie Redmayne vs. John Legend

Eddie Redmayne

Eddie Redmayne looks so consistently stylish thanks to his commitment to classic pieces. Chinos, simple sneakers, and a denim jacket are the foundations for a great casual outfit, but when he does get red carpet ready, he keeps his cuts slim and simple, mixing things up with pattern and color.

John Legend

John Legend knows the value of a statement piece, and especially a statement jacket. Outerwear is the first part of an outfit that a stranger notices, and Legend knows it’s the part of your outfit worth making (bah-dum-ching) legendary. He also knows the flattering effect of wearing one color head to toe, whether it be all black everything or a bright blue suit with matching shirt.

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Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.