Round 1 of SG Madness 2018: 7 VS 10 and 2 VS 15 | Style Girlfriend
Round 1 of 2018 Men’s Style Madness: 7 VS 10 and 2 VS 15
A former president vs. a former Final Four-er

By Style Girlfriend | Last Updated: Mar 11 2019


It’s the final day of SG Madness 2018, Round 1! You know the drill by now: choose the most stylish guy in each match-up just by clicking on their name–no login required. Now lesssgo!

7 vs 10


Justin Trudeau

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1 | 2 | 3

The Canadian prime minister is known for his strong sock game, but that doesn’t mean you should sleep on the rest of his wardrobe. Professional yet modern, classic and interesting, Trudeau is leading by example that just because you wear suits to work doesn’t mean you have to dress boring.

Jordan Peele

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1 | 2 | 3

Our love for Jordan Peele is very real, but it wasn’t until we started digging into his red carpet and off-duty looks that we realized: the guy’s also got style for days.

From hip sweaters to that fire engine red DB at the Independent Spirit Awards, we now look forward to his next look as much as we do his next movie.

Justin v. Jordan

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Antonio Brown

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1 | 2 | 3

Is Brown’s personal style for everyone? No, but the Steelers wide receiver and DWTS alum pulls off every look he wears with confidence, which counts for a lot. writer and GMFB contributor Adam Rank concurs. “Antonio Brown is the best WR in the last 20 years (don’t @ me), and it’s fair that he dresses accordingly. He definitely pushes the boundaries and comes close to going out of bounds at time, but he always hits that toe-drag swag to look pretty dapper.”

Alex Rodriguez

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1 | 2 | 3

The J.Lo bump helped catapult Alex Rodriguez into SG Madness for the first time this year. We love his Miami business executive who is constantly on a working vacation look. It just really works for us (or maybe we just need a working vacation).


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John Legend

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What can we say about John Legend that we haven’t said before? The man can dress, y’all!

Kelly Slater

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One of the older guys to make his first appearance in this year’s SG Madness bracket, the 46-year-old Kelly Slater surfed onto our style radar with his clothing company, Outerknown. The surf-inspired apparel has a distinctly laid-back feel to it that we love, with blanket shirts and trunks (natch) that are total standouts.

Legend v. Slater

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Roger Federer

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1 | 2 | 3

Roger Federer is your friend’s dad who always looks great, whether he’s showing up to your Saturday morning basketball game in a Harrington jacket, dark jeans, and desert boots; or dashing out the door for date night with the missus in a blazer and artfully-unbuttoned OCBD right when you come over for a sleepover.

What? No, we’re not thinking of anyone specific. Why do you ask?

Look, the point is…is his style super-exciting and “out there?” No, but cool dads don’t need to look “out there” to look…well, cool.

Virgil Abloh

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1 | 2 | 3

The hyped designer behind of-the-moment label Off-White couldn’t be a better advertisement for his particular brand of elevated streetwear.

If the man can convince us to dig out our old fanny packs and wear them in 20-freaking-18, you know he must be doing something right.

Federer v. Abloh

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2 VS 15

men's style madness, style girlfriend, jfk, kennedy, march madness, unilever

Stranger Things Kids

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1 | 2

We admit it: the four child actors from Stranger Things should have made this list last year. Ever since the show premiered, Gaten Matarazzo (Dustin Henderson), Finn Wolfhard (Mike Wheeler), Noah Schnapp (Will Byers), and Caleb McLaughlin (Lucas Sinclair) have been showing up everywhere from talk shows to awards shows looking fly af.

For now, we’re entering them into SG Madness as a group, but if they keep this up, don’t be surprised if you see them get seeded on their own soon enough.

Prince Harry

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Here’s the thing about Prince Harry—like, yes, he’s literal royalty, but his wardrobe? It’s 100% attainable by decidedly non-royal folks, just like you. And, okay, us. (FOR NOW).

His favored topcoat? Club Monaco. The shoes? Cole Haan. Just call him the People’s Prince.

The Kids v. The Prince

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Cole Sprouse

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1 | 2 | 3

Hey, do you watch Riverdale? COOL, US EITHER. We also didn’t watch The Suite Life of Zach and Cody (it came out a little after our time), but that hasn’t stopped Cole Sprouse from hitting our style radars like Whoah recently.

The actor/photographer/celebrity twin isn’t afraid to take chances on the red carpet, and while some of his looks veer a teensy bit retro for our tastes, we like that he’s putting himself out there in a way a lot of younger guys just don’t have the confidence to try.

Donald Glover

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1 | 2 | 3

Like Harry Styles, Donald Glover is having a Fashion Moment™ this year, and we here at SG HQ are all here for it. As excited as we are for the return of Glover’s FX show Atlanta, we’re even more excited to see what the artist still-but-soon-to-be-formally-known-as Childish Gambino shows up wearing for the Star Wars franchise’s Solo press tour. Because you just know it’s gonna be good.

Sprouse v. Glover

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Justin Timberlake

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1 | 2 | 3

Okay okay, so this pick might be a little…problematic. Our team was not a fan of Timberlake’s Super Bowl camo suit, (designed by Stella McCartney!), but we loved that red scarf and unexpected brown lace-ups at the Brit Awards, above. And…y’know, it’s Justin.

Ultimately, we felt he deserved a slot. Especially with a new album out and tour just getting started, we know we’ll see a lot more of him. And hopefully, we’ll like what we see. That said, it’s up to you to see how far the former N*SYNC’er goes this year.

Dave Franco

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1 | 2 | 3

Remember what we said about those accused of sexual harassment not getting seeded? Yeah, say hi to first-time SG Madness contender, Dave Franco.

JT v. DF

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Barack Obama

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1 | 2 | 3

Looks like 44 left all his ties in the Oval Office. We like the dressed-down dad vibes; we also just like seeing him around. But he’s got some competition right out the gate, in the form of…

Ryan Gosling

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1 | 2 | 3

Perennial Final Four-er Ryan Gosling is Gabi’s pick to go all the way this year. Will she be proven right, or will the Gos fall to the (former) prez? Only you can decide.

Obama v. Gosling

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