Who is the Most Stylish Internet Entrepreneur?

Tech Titan Style War: Mark Zuckerberg vs. Jack Dorsey

On the scale of Silicon Valley stylishness, Twitter cofounder Jack Dorsey is the aspirational apex. He's set the bar for a debonair new breed of Web entrepreneurs, helping to move the public conscious away from the nerd archetype that preceded it. And he stands in direct opposition to the disheveled, hoodie-wearing, man-boy persona typified by Mark Zuckerberg.

PLUS: A Guide to Summer Shorts

Well, early Mark Zuckerberg, at least. A decade after founding Facebook, the guy has cleaned up his act considerably. Now beholden to stockholders, and a year shy of his 30th birthday, he's finally dressing like the grown man he is, as this picture from his trip to South Korea demonstrates. But he's still no Jack Dorsey.

PLUS: The Shoes Every Man Should Own

For this occasion we're happy to unveil the The Jack Dorsey Style Scale™, a highly scientific way to rate Internet moguls' approach to dressing relative to that of Dorsey's. Zuckerberg's score? Just two Dorseys out of five. While we give him credit for at least trying on his trip East, the man has broken our number one commandment: Thou Shalt Have a Suit That Fits. His jacket sleeves are baggy, the shoulders are droopy, and he's committing the cardinal sin of having both buttons buttoned. There's too much shirt collar showing, but not even a hint of cuff. The tie is too loose and, hold on, is he wearing a black suit?

We're being nitpicky, yes, but men's-wear is all about the details. And if there's anyone who can afford a nice suit and a decent tailor, it's Zuck. Somewhere in the world, Jack Dorsey is pasting this photo in his Mark Zuckerberg burn book - and we don't blame him.

More from Esquire:
The Best Dressed Men of All Time
15 Great Polo Shirts for Under $100
15 Things Worth Splurging On, and Why