Style

Men's Style Madness: Round 1, 8 VS 9

Singers and Silly Somebodies

You made it to the end of Round 1 – congrats! Round 2 starts tomorrow at 8AM so we (and only half the contenders!) will see you there.


This tournament is brought to you by the custom menswear experts at IndochinoWhy custom? Because nothing looks or feels like clothing made just for you. Join the ranks of these stylish competitors today.


 KENNEDY REGION

Drake VS Nick Wooster

DRAKE

Drake threw shade at fellow first round contender -and pal – Kevin Hart, and while we respectfully disagree (Kev4Lyfe), we like that he cares enough to comment. He’s also not afraid to rock an espadrille in the summertime, though he tends toward all black everything, along with the occasional dose of camo, much like his competitor below.

NICK WOOSTER

Dubbed “the Alpha Male of American Street Style” all proper #menswear aficionados are familiar with Nick Wooster’s body of work. His style is definitely part of the fashion class, with no look completely off limits. He’s worn color block pastel jackets, cargo shorts with a blazer, an a short suit – all with ease and confidence.

…DRIZZY OR WOOSTER?

McQUEEN REGION

Bruno Mars VS Jason Sudeikis

BRUNO MARS

What Bruno Mars hasn’t told anyone is that “Uptown Funk” was originally the way he described his personal style. We’ve gotta give it up for Mars as one of the few modern musicians who can wear a fedora and make it look good, and – more impressively – that he can do so while wearing a leopard blouse unbuttoned to there with a necklace and look totally handsome AND manly.

JASON SUDEIKIS

Jason Sudeikis is equal parts SNL alum and total sneakerhead. He’s one of few adults who can pull off sneakers with a suit, and he’s totally cool with loud pops of color which we at SG HQ adore. He (well, lady love Olivia Wilde) had a baby this year, so he’s also a new member of the cool dads club.

…HAT HAIR OR SNEAKERHEAD?

BASQUIAT REGION

Pitbull Vs Aaron Schock

PITBULL

Pitbull is the beating heart of menswear in Miami: white pants, rolled at the ankle; white loafers with no socks; bright colors on top and bottom. Definitely flashy, always confident, always surrounded by women.

AARON SCHOCK

In Schock-ing news, (how could I resist?!) Aaron Schock resigned just yesterday for a “spending scandal” which allegedly included using taxpayer dollars on a Downton Abbey-inspired office and probably hitting up Tommy’s Closet for some sweet threads like that pink tie.

…MIAMI OR MIDWEST?

**note names in poll are reverse of image..choose carefully!

BOND REGION

Conan O’Brien VS Jeff Goldblum

CONAN O’BRIEN

Conan is the giant leprechaun of late night television and I was very excited to type that because I love alliteration. He also knows the benefit of complementary colors, and often chooses blues to set off his brightly glowing red head of hair. Oh, and that leather jacket? He pulls it off way better than Leno ever could.

JEFF GOLDBLUM

Gabi says: “I know Jeff Goldblum from Portlandia, but he’s been in several other more influential things that just don’t overlap with my niche television and movie choices, including The Fly and Independence Day. Also worth noting is how many pairs of cool glasses Goldblum has – probably more than the shoes I have in my closet (and that is a double digit number).”

…’BLUM OR ‘BRIEN?

You have until 9PM EDT tonight to get your votes in – and to tell us who should advance to Round 2!