Style

Men's Style Madness: Round 1, 7 VS 10

Almost Exclusively Actors

You made it to the second to last set of the first round! Can you believe it?


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


 KENNEDY REGION

Ryan Gosling VS Matthew McConaughey

RYAN GOSLING

Where do we even start with RyGos? Well, he got his start as a member of the Mickey Mouse club with fellow contender JT, so there could be a Mouse House Face off if we play our cards right. He also had a baby this year which lands him in the “cool dad” category. His personal style was once described as “subversive,” which I think is maybe the wrong word, but they definitely meant it in a good way, so we’re cool with it.

MATTHEW McCONAUGHEY

Do you guys remember this SG style moment with Mr. McConaughey and RyGos? It’d be a lot cooler if you did. McConaughey-hey-hey may be the most crunchy-granola challenger in this year’s Men’s Style Madness Bracket, with an appropriately laid back style to match. His suit game in recent years, however, has been quite flashy, with lots of colorful numbers, as shown above and below.

…HEY GIRL OR ALRIGHT, ALRIGHT, ALRIGHT?

McQUEEN REGION

Jake Gyllenhaal VS Idris Elba

JAKE GYLLENHAAL

Jake Gyllenhaal started as an angsty teen in a hoodie and a skeleton suit but as he’s grown, so has his style. He cares equally for suits and sneakers, facial hair and free flowing, man-bun locks. His father was a Halloween master that we can all aspire to be with our own kids, and which, we imagine, may have had some impact on Jake’s decision to stick to simple, tried and true style choices as an adult.

IDRIS ELBA

It’s almost a joke that Idris is the lower seed of this match, because he is seriously seed-1 sharp. Where are your Twitter followers, Idris!? His attention to detail and penchant for color make an upset this round nearly certain, purely based on statistical figures.*

*e.g., the comments on the Selection Sunday post 

…JG OR IE?

BASQUIAT REGION

Jack Dorsey VS Liam Hemsworth

JACK DORSEY

Jack Dorsey is the “Twitter guy” – as in, a co-founder of Twitter. Style isn’t generally the first thing on tech guys list of t0-do’s – as shown by the characters of Silicon Valley (tangent: Have you guys seen that show?! Amaze.) – but Jack Dorsey makes an effort and opts for slim fitting suits and jeans as opposed to cargo shorts. So even if he does hide behind his computer screen all day, chances are he’s lookin’ good.

LIAM HEMSWORTH

Wait, didn’t we already see this name on the bracket somewhere else? Yes, we did (and you voted for or against him already, right?). The Hemsworth brothers are all well dressed, but just because one’s older, or one wears khakis better doesn’t mean we shouldn’t give the other a chance. Who knows, it may even come down to them duking it out for the bottom half of the Basquiat Region – we’ll see.

…TWEET TWEET OR MILEY’S EX?

BOND REGION

Roger Federer VS Adam Scott

ROGER FEDERER

This tennis player is beloved by Vogue editor Anna Wintour, and that can only mean one thing – man’s got style (also, she loves tennis, but let’s not factor that in here). His choices are classic and his suits well-cut, with no obvious missteps, except for maybe playing it safe to often. But this isn’t Project Runway so we’ll just accept that he’s generally dressed pretty sharp, but enjoys his top button undone pretty often, thank you very much.

ADAM SCOTT

What was in the water over at Parks & Recreation? Scott is our third contender from the recently-ended sitcom. While Ben Wyatt was an unlikely style icon, his nerd-chic style captured a lot of viewers’ attention, and it seems the actor’s personal style isn’t far off. That natty suit in the middle? Yes please. A sportcoat with elbow patches? That’s a Cones & Dunshire Maverick move if we’ve ever seen one.

…TENNIS OR CATALINA WINE MIXER?

Vote in before 9PM EDT tonight – and sound off in the comments!