Caleb Williams Is Reaching Icon Status With Latest Honor

The Bears' quarterback is keeping it cool both on and off the field.

Jan 20, 2026; Chicago, Illinois, USA; Chicago Bears quarterback Caleb Williams, left, and Chicago Cubs outfielder Pete Crow-Armstrong are seen during the first half of the game between the Chicago Bulls and the LA Clippers at United Center. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images

For the second year in a row, Caleb Williams has proving himself the best in the league—at styling on everyone.

On Monday, Williams kicked off Super Bowl week with some more (figurative) hardware in his trophy case, having been voted GQ’s 2026 Most Stylish Football Player. (If you’re only just finding out this make-believe award exists, you’re not alone.) 

The second-year Bears quarterback knocked off a slew of contenders, including two of his own teammates (Rome Odunze and Jonathan Owens) and the ever-fly Stefon Diggs to repeat as GQ’s swag champion. Since I’m not a style person myself, let’s let GQ explain what made Caleb so elite in the aesthetic department.

“Williams turned heads this year with a combination of approachable-yet-swaggy normcore and elevated streetwear. One day, he’d be rocking a Polo Ralph Lauren sweater vest over a plain white T-shirt and simple light-wash jeans. The next, a Vanson Leathers x Supreme jacket. Somewhere along the way, he found time to implement a brat green cardigan, a perfect match for his signature matcha. The king of wired headphones, painted nails, and Houdini-like pocket maneuvers is, once again, also the king of NFL fashion. Take a bow, Caleb,” wrote Matthew Roberson.

While I’m not exactly a follower of the fashion scene, I can say one thing: Williams seems to have a very clear sense of what he likes and how he sees himself. And that actually ties directly into what has helped him become one of the NFL’s most electrifying players.

Williams' sophomore season with the Bears showed definitively that, while he can still improve, he’s made major strides as a pocket passer and general of the Bears offense in his first year with Ben Johnson. But he also retains his own personal genius as a player, busting out the most insane plays we’ve ever seen from a Bears quarterback. 

Through it all, he has never stopped being himself: from the matcha/headphones combo to the designer fits and nail paint. 

Last year, those things made him a target for detractors, who either criticized him for not focusing enough on football or straight up calling him un-masculine. Not only did he give give precisely zero [bleeps] about that, he kept doing it and took his game to another level, forcing the haters to eat whole plate-fulls of crow.

The cool part: his authenticity is resonating beyond Chicago, vaulting him into the conversation for one of the NFL’s most recognizable stars. Like other contemporaries, he proves you can dominate on the field while making a statement every other day of the week (and right before the game, too.) In doing so, he's helping redefine what it means to be an NFL star.

And we can’t wait to see him go for the three-peat next year.

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