Men's Style Madness

Round 2 Men’s Style Madness 2018: 3rd heat

Calling all your hot takes

By Megan Collins | Last Updated: Mar 11 2019

We’re almost through Round 2 of SG Madness 2018! You know the drill: in each matchup, vote for the most stylish male celebrities…according to you, that is.

Today’s winners move on to next week’s Style Sweet Sixteen.

So, who ya got?

Darren Criss vs. Harry Styles

Darren Criss

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Gotta say, this is a matchup I did not see coming. Nothing against either of these very talented, and very stylish celebs, I just…didn’t know you all would connect with them both so strongly. That said, who will emerge victorious from this face-off? Darren Criss, or…

Harry Styles

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Harry Styles? Their looks are sooooo different, so I have a feeling it won’t be close; I just for the life of me don’t know which way it’s gonna go.

Criss v. Styles

John Legend vs. Dave Franco

John Legend

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Ooooh. Oh boy oh boy oh boy. I am going to have a VERY hard time pulling a lever on this one. I love me some John Legend, and appreciate all the fashion risks he takes. He seems very comfortable dressing up in a way that some guys might find stuffy or “trying too hard” (I hate that phrase), but I think he just likes looking nice.

That, and I bet Chrissy is all, “Ooh baby, you look cute today!” and he’s all, “Cool, I’m gonna dress like this every day. Done.”

Dave Franco

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Of course, Dave Franco has his own style cheering section in wife Alison Brie (I mean, I’m guessing…I can’t imagine every time they’re about to leave the house, she’s all, “Ugh, you’re wearing that?”). And I really like her. I never watched Community but I did like the scene in one of the first couple episodes of Glow I watched before I lost interest, when the main guy was all, “I can’t decide if you’re attractive or not, and if you are, what kind of attractive you are,” and I’d never felt more seen because I look in the mirror and think that too, sometimes.

Anyway, where were we? Right, I actually really like [Dave] Franco’s style. He’s like a grown-up hipster that I don’t want to punch in the face, and for that, I’ve gotta give him credit.

Legend v. [Dave] Franco

Milo Ventimiglia vs. Kit Harington

Milo Ventimiglia

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Bad boys, bad boys…whatcha gonna do? Whatcha gonna do when they face off in Round 2 of SG Madness and you have to pick just one even though you like them both, and you bet that if they got into one another’s closets, a lot of the same stuff would fit and maybe they could do a Freaky Friday-style wardrobe swap and that would be really fun?

Kit Harington

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…Or, I suppose you could just judge Milo Ventimiglia and Kit Harington on the merits of their personal style, as is. No Freaky Friday-induced style swap, and that would work, too.

Up to you, really.

Ventimiglia v. Harington

Roger Federer vs. Ryan Gosling

Roger Federer

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To review = Cool Dad

Ryan Gosling

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And = Gabi’s pick to take the whole damn enchilada.

So, guys. Who’s it going to be?

Federer v. Gosling




 Justin Trudeau vs. Prince Harry

Justin Trudeau

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Oh, well this is interesting. Are you going to advance a head of government?

Prince Harry

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…or a head of state? Well, Harry’s not really the head-head of state. His grandma is. But like, he holds a ceremonial position in which he represents the country in a similar manner as the Queen…ah, never mind. You get where I was going with that.

Justin v. Harry



Alex Rodriguez vs. Donald Glover

Alex Rodriguez 

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Wowowoww. Okay, this might be our most distinct matchup of the day, from a personal style perspective (and isn’t that what all of this is?).

I’m so so so curious to see who you vote through to the Style Sweet Sixteen from this faceoff. The A-Rod (A.Rod? ArOd?) love has been strong so far, but will it be stronger than your heart eye emoji love for…

Donald Glover

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…the artist formerly known as Childish Gambino? Man, if I were a betting woman….actually, I wouldn’t tell you, because that’s how bets work. Or is that just poker? I guess it’s clear by now that I’m not a betting woman, so I’mma just step aside and let y’all do your thing and vote.

Rodrigquez v. Glover