The Most Stylish Guys of all Time

50. Fats Navarro
Occupation: Musician
Approximate Weight: 200+ lbs.

Although his time on the planet was brief, the trumpeter made a profound impact on the jazz world. As such, he was regularly decked out in some pretty great suits and tucked in shirts. Yes, it was the '40s and just the norm, but you can't say he would look out of place in the context of today's stylish guys either. Whether tooting his horn in untucked button down shirts or looser, double-breasted suits, Fats Navarro certainly looked good doing his thing.


Most people think fat guys and fashion have nothing more in common than the letters "f" and "a." For too long, best-dressed lists have been cluttered with stick-thin men who look like their idea of indulging is a juice cleanse and a rice cake rather than a burger and a milkshake. Nah, fuck that.

Big dudes have a hard enough time finding clothes that fit without having to get things custom, and many attempt to hide their weight through even baggier clothes. This list is praising the guys who embrace their size and wear it proudly underneath garments that fit great and look awesome—redefining what it means to "push weight." We're tipping our hat to the historical heavy-hitters whose style takes the cake—and who would probably eat that cake, too.