Who is the Most Stylish Man of 2019?

Who is the Most Stylish Man of 2019?

Choose your fighter

By Megan Collins | Last Updated: Mar 4 2024 | 3 min read

Happy SG Madness 2019, everybody!

sg madness 2019

While anxious college athletes (and the fans who love them [but don’t necessarily want to see them paid]) awaited their fates on Selection Sunday, our team was hard at work putting the final touches on this year’s SG Madness tourney.

How it works

If you’re new here, a quick explainer. Every year, our team huddles up to select the year’s most stylish men from music, movies and more. From there, it’s up to you, the Style Girlfriend community. You decide who gets crowned the most stylish man of the year. For the next three weeks, vote your favorites on through the single-elimination tourney.

(We retire winners, which is why you won’t see well-dressed folks like Ryan Gosling, Ryan Reynolds, and Jeff Goldblum in the bracket below.)

To shake things up, we seeded contestants a little differently this year. More below on how we sorted them into newly-formed, and admittedly imprecise, buckets according to their personal style predilections.

Here’s what you need to know about the SG Madness 2019 breakdown:


In the top right, you’ll see the “Fashion-Forward” bracket. Here you’ll find the celebs who aren’t afraid to push the boundaries of what looks good in favor of what looks cool. Sometimes it works, sometimes it doesn’t, but you’ve got to admire their willingness to try new looks and trends.

Folks at places like GQ would call them “swervy” or “wavy” or some other word we’d be afraid to say out loud for fear of using it wrong. You can just call them trendy.


Continuing counter-clockwise, is SG Madness 2019’s “Fancy” bucket. This means…pretty much exactly what it sounds like. These are the guys who somehow look more comfortable in a tux than they do in sweatpants. Kings of the red carpet, these guys bring style and ease to dressing up.

Even in off-duty looks, good tailoring and attention to detail lets you know their outfits came together with the same careful planning as their Oscars lewk.


In the bottom left, you’ll find the “Classic” bracket. These guys might not be breaking any new ground when it comes to fashion trends, but they always show up—to the red carpet, to interviews, to the airport—looking stylish and well-groomed.


And finally in the top left, this year’s “Committed” bracket. A nod to both our theme this month, and the recognition of how personal style can go beyond neat categorization, this bracket includes an array of celebs whose fashion sense on its face doesn’t seem to have much to do, one with the next.

What they all have in common? They’re seriously committed to their personal style.

Styles which are, well, pretty wildly different one to the next. While Jason Momoa and the Hemsworth brothers have little in common apart from a love of rugby (I’m guessing, anyway), they’re alike in how committed they are to their looks. In Momoa’s case, that’s haute couture caveman, and for the Hemsworths, it’s…well, it’s pretty much henleys.

And they all look great in whatever it is they love to wear, hence their spots in SG Madness 2019.

Below, the 64 contestants in this year’s SG Madness 2019:

SG Madness 2019, most stylish man 2019

All week, be sure to weigh in with your picks before voting for this round closes at 5pm ET on Saturday, March 23.

Check out all 64 contestants (I’m pretty sure you can open the image in a new tab to view the full-size version), and then tell me:

Who are you picking to go all the way?

And which first round match-up do you think will be closest?

I started Style Girlfriend to help guys look, feel, and act their best.