The problem is that, in addition to what I've already said, the essay itself does not do a good job at making a point. Sure, it gesticulates at some points. Sure, you could assume the author is trying to say X, but I think that is one's own projection of the essay's vague intent. In fact, we have two comments here which potentially illustrate what I mean. You argue that the article is about fashion. Someone else argues that it's about social privilege. I argue that it's so vague that it's really about nothing.

I'm not sure who you're calling a "critical-thinking-by-the-numbers guy," but since I was one of those criticizing the article, I'll respond that it is wrong of you to assume that our criticism must be due to the fact that we/I don't understand that fashion in some ways represents who we are. Because I certainly recognize that fashion represents not only who we are, but who we want to be. But that does not absolve the article of having made no meaningfully substantiated conclusions apart from interesting points about the anonymizing use of hoodies.

If you asked me, the only reason Zuckerberg wears/wore hoodies is because he is/was a twenty-something. In his case it has nothing to do with anonymity/surveillance, etc. etc. They're just what was in fashion when he was in college. They're still in fashion. I wear them. They're comfortable. For youth, they're not uncool to wear. A suit would be uncool. Imagine all the grief you'd get if you wore a suit to high school.

EDIT (reply to below): While your reply may or may not be accurate, I think the fact that this is yet another interpretation of what the author's point makes my argument even clearer, that the essay has no point at all.