Men’s Style Madness 2018: Sweet Sixteen

Men’s Style Madness 2018: Sweet Sixteen

Actors and Princes and Athletes, Oh My

By Megan Collins | Last Updated: Jun 23 2022 | 8 min read

Wowowow! We’ve made it to the Style Sweet Sixteen; can you even? These are the best dressed male celebrities, as voted on by you. Who will make it to the next round?

I’m  not gonna lie; this isn’t going to be easy. By now, we’ve weeded out all the “Should they have even been seeded?” on-the-style-fencers. At this stage, very guy below is here because he absolutely deserves to be.

So, who will make it on to the Elite Eight of SG Madness? Cast your votes below.


Sterling K. Brown vs. Michael B. Jordan

Sterling K. Brown

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I’ll be honest; one Megan K. (the K is also for Kathleen, interestingly enough!) Collins is pretty psyched that Sterling K. Brown made it this far.

As someone who only recently became obsessed with This Is Us and Brown specifically, I didn’t know how many people were on the SKB bandwagon with me.

As it turns out, plenty! The respect is well-earned; the actor always shows up places looking like he truly enjoyed the process of getting dressed. While his style is on the safer side, he’s also a little older than some of his male peers on TV and in movies, several of whom made this year’s tourney! Such as…

Michael B. Jordan

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My pick to go all the way, one Mr. Michael B. Jordan!

And that’s where things get tough, right? Brown has found himself facing off in the Style Sweet Sixteen against his Black Panther co-star, who also shows up to events looking dressed-with-a-capital-D.

While they both look great, it’s arguable—or at least, I’m arguing—that Jordan takes some more chances with his style, which winds up rendering his style more interesting. Again, that’s me talking, so do with my opinion what you will.

Brown v. Jordan

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Armie Hammer vs. Prince Harry

Armie Hammer

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Taylor’s pick, Armie Hammer has squeaked his way into the Style Sweet Sixteen, with a narrow victory over Chris Paul in the last round.

It seems that what Hammer has going against him is the same as what’s kept him afloat in show business even after his commercial success seemed less viable – his stupid-handsome goo looks.

In the last round, someone made the point that it’s basically impossible to judge his style because he’s coasting on his looks. To which I say, yeah, but there’s a lot of handsome guys who didn’t make SG Madness.

So, don’t discriminate against Hammer just because he looks like a Ken doll come to life. Judge him on his personal style. And consider it against…

Prince Harry

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In my mind, what’s carried Prince Harry this far is he might have the most accessible personal style in the whole SG Madness bunch. And that’s saying something, considering he’s a freaking prince.

He dresses the way I think plenty of Style Girlfriend readers in their late twenties and into their thirties would like to look most of the time – pulled together but always comfortable. Lots of flattering topcoats. Lots of shoes you can dress up or down.

Is it super-adventurous? No. Does it work for him, and plenty of others like him (well, not like him like him..)? Absolutely.

All that, plus let’s not act like Meghan Markle isn’t helping. If ARod got a JLo bump this year, I’d say it’s pretty clear the younger Windsor is definitely getting some hi-vis shine from his super-stylish (and stupendously-monikered) future wife. It all adds up to a Moment™ for Prince Harry.

Armie Hammer v. Prince Harry

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Idris Elba vs. Hasan Minhaj

Idris Elba

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My best friend texted me at an extremely rude hour recently to let me know Elba’s showdown with Lebron James in the second round was too close for her liking. No bother that Elba took 82% of the vote in that faceoff.

“He should get everyone’s vote!”

Okay then.

Now that you know where Tall Megan stands, what say you in the Style Sweet Sixteen matchup between Elba and….

Hasan Minhaj

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I’ll be honest: I loved seeing the comedian (and future talk show host) beat Ansel Elgort in the last round. There, I said it.

Has he met his match in Elba, though? If it were just up to Tall Megan, the answer would be yes. What say you, though?

Elba v. Minhaj

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Dwyane Wade vs. Donald Glover

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One of only two athletes still standing in SG Madness, Dwayne Wade beat surprise contender race car driver Lewis Hamilton in the last round to make it here. I love D.Wade, but I’m a little skeptical that we’ll see this otherwise strong player in the Elite Eight, considering he’s up against…

Donald Glover

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The future Lando Calrissian can do it all. Unexpected style on the red carpet (grandpa cardigan or off-white dinner jacket? Get you a Glover who can do both!), to looking effortlessly cool picking up groceries, this guy just gets it.

So guys, who’s it gonna be?

Wade v. Glover

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Joel Edgerton vs. Malcolm Jenkins

Joel Edgerton

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Okay, I just have to get something off my chest. I don’t think I’ve ever seen Joel Edgerton in anything, apart from great clothes on the red carpet.

Don’t get me wrong; the …American (British? dunno, and not gonna look it up) actor has great style (AND/OR IS WORKING WITH A STYLIST HE TRUSTS TO DRESS HIM…DON’T @ ME); I just don’t think I’ve ever seen any of his movies. He’s a movie star, right?

It’s funny. He got seeded so high because he has an insane following on Instagram, and because, yes, the boy can dress; I just didn’t realize he’d go so far in SG Madness, because his brand awareness is so low for me, personally.

But this isn’t about me. It’s about you guys. And if you think Edgerton can outdress…

Malcolm Jenkins

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Here at SG HQ, everyone’s pretty psyched for the Eagles’ Malcolm Jenkins. First the Super Bowl, now a place in the SG Madness Style Sweet Sixteen? I know, I can’t say for certain which he’d label as a bigger deal, either.

Since we’re at the point in this competition where I’m improperly comfortable letting you know what I think and trying to sway your vote, I’ll direct you to Damari Savile, the Philadelphia menswear store founded by Jenkins. For those who like to argue in favor of those contestants with an inherent fashion sense. Just, y’know, in case you were wondering about his style bona fides.

But that’s all I’m going to say about that.

Edgerton v. Jenkins

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Darren Criss vs. John Legend

Darren Criss

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Since we’re being honest, I’ll tell you that Darren Criss is another SG Madness contender I didn’t expect to see go this far. If Sterling K. Brown’s Cinderella story run is any indiction, maybe you guys are just really big American Crime Story fans?

So, will you push Criss through to the Elite Eight, or will he finally fall to…

John Legend

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Legend is playing the lead in this Sunday’s Jesus Christ Superstar live musical event, not that that’s a reason to vote for him (or against him, obviously), but he might be tough to beat when he’s got God on his side. I think that’s how this works?

Criss v. Legend

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Chadwick Boseman vs. Chris Pine

Chadwick Boseman

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Will my prophecy of a T’Challa v. Killmonger championship come to be? Only you can decide.

Chris Pine

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First, you’ll have to push Boseman past Chris Pine, an affable-seeming movie star who can’t help but show up in fits that are unfailingly #SGapproved.

I know! Argh, what to do? I told you this wouldn’t be easy…

Boseman v. Pine

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Kit Harington vs. Ryan Gosling

Kit Harington

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Look, I don’t watch Game of Thrones, and that’s…well, probably not going to change anytime soon (along with The Wire, it’s my “Maybe if I get my wisdom teeth and I’m really hard up for some binge watching” show…), but that doesn’t mean I can’t appreciate Jon Snow’s personal style.

I want to attribute it to his British-ness, but of course, there’s more to it than that. He’s on the more slight side, which sinks some guys’ style. Not Harington; he’s learned the importance of a good tailor and he keeps things simple. Like, really, really simple.

Which I’m curious will be enough to grab your vote over a slightly flashier dresser, in…

Ryan Gosling

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Man, I’ve really wanted to blow up Gabi’s spot for choosing Ryan Gosling to go all the way this year, but I’m starting to come around to this cunning pick. After all, the Gos blew Roger Federer out of the water in the last round and has maintained a comfortable victory over all his other competitors so far (including 44, who I thought might go farther this year).

Has he met his match in the Style Sweet Sixteen? We shall see.

Harington v. Gosling

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