Is it possible that the modern adopters of this look are calling back to this as a touchstone, perhaps in memory of weird uncles or older brothers?

Also, relative to the endless nice guy/creep thing, DAMN MY LIFE IS GREAT. WHEN DID THAT HAPPEN.

I know I’ve had periods of fitting into one or the other of the categories you’ve listed. I think that suffering from a “nice guy problem” (whichever one fits) is not a permanent state. The conception of “why” it’s a “problem” becomes more sophisticated as we age, hopefully, and eventually it ceases to be a “problem” at all.

Because it’s okay for gay men to be a little fem.

I can’t say that I’ve observed that since c. 1975.

What I see getting unfortunately lumped in this messaging is the surfer/skater trilby with an appreciation of 50s vacation culture and good hearted geek/nerds that loves trench coats and noir imagery. In my opinion it’s easy to hate on the nerds and unwarrantedly insensitive. As far the youthful surfer trilby surfer/skate culture, if the person has the character associated with the hat, they won’t care if a bunch of random internet people want to date them or not. Chances are they wouldn’t be on OKC anyway.

If I have to fall on one side of the fence, I think it has to be pro-fedoras. Projecting your feelings onto a group of people is never a great thing, even if you can usually understand the sentiment. The fedora mocking is really petty though, and it’s coming from an ugly place, and it’s being sanctioned by a number of people who should be able to sympathize with being humiliated, insulted and put down.

Having said that, taking pictures of yourself always teeters dangerously close to lameness, so it won’t hurt you to not have pictures of yourself in a fancy hat floating on the webs.

You’re totally failing to address the social aspect of what precise rights “looking awful” gives you or others to behave in a rude fashion towards them. Even if the combination of, say, two clashing colors offends your sensibilities in some manner, the offense is still very subjective and the response is still socially constructed. The very notion that wearing two clashing colors — or “looking bad” at all — is opprobrious to the point of deserving mockery is what I’m trying to attack. 

So yes, I have a persecution complex about people being attacked for what they’re wearing. Why? Because I’ve had some very dear friends attacked for what they were wearing. Reality matching up to your fears will give you issues that way. 

But the bit about the “cool kids” was just an attempt at playful sarcasm. I like sarcasm. Example: “Thank you so much for having given me the benefit of the doubt, Thomas.”

I like my hats, but I’m not a guy, so I suppose all the hate doesn’t really apply to me – although actually I mostly wear my hats when I’m dressing like a guy (dapper butch me) and sometimes I get “sirred” when I do.  

I think what gets me about this article – and a lot of these comments – is the level of fashion policing going on.  I might like or not like someone’s style choice, and I’ll admit sometimes I can get fairly snarky about it, particularly if they’re being an utter ass.  (That asshole preacher the other day – why did he think saddle shoes were a good choice with his ensemble?)  But usually, if someone thinks they look good, I’m all for it.  People can wear the most ridiculous things, and if they’re happy about it, so am I.  The woman at the airport in red skinny jeans, a chartreuse short corduroy jacket, peacock-blue top, and bright orange scarf?  She looked awesome!
Last year, in addition to fedoras, I had a lot of fun wearing multiple plaids.  It was a game: how many forms of plaid can I wear at once? (Socks, shirt, coat, hat, gloves, scarf.) This year, while multiple plaids are still kicking around in my thrift-store-eclectic and gender-complex wardrobe, I’m enjoying mismatching patterns:  plaid with argyle with stripes, generally.  I am not doing this to look cool; my default assumption is that if I do something it is automatically Not Cool (although a batch of Terribly Cool people in mismatched plaid walked past me the other day, confusingly).  I just like to amuse myself with my version of Not Cool.  

I can’t really buy the fedora = Entitled Nice Guy thing. I mean, geekdom is chock-full of Entitled Nice Guys, so if geek guys are wearing lots of fedoras, there you have it…  but it’s not the hat that should take the blame.If my hat and other fashion choices screen out people I wouldn’t want to date because OH GODS THE JUDGEY, I suppose that works out well.  So far I end up dating people who look at my sometimes rather strange outfits and think I look fun and interesting. 

I’m sure there’s a lot of 80s high school drama villains who agree that being socially awkward is enough to merit the condescending tone and derisive attitude, but in the real world, that’s just mean.

Your taking the most stereotypical anti-geek stance ever portrayed in popular culture, with the added benefit of singling out an arbitrary sub-group aside, let’s examine your actual claims.
You tell about the ‘forever alone’ jokes, the ‘no women on the internet’ meme. Yeah, those exist, no wonder, and in all fairness have some basis in truth: among my friends, their degree of geekiness has always been inversely correlated with the ease with which they make any romantic connections.
And yes, female geeks were, historically, comparably rare, and in my direct environment still are. Does that mean I’m hostile to any females who self-identify as geeks? Of course not, the fact there are fewer geeks doesn’t mean that’s something any male geek experiences as desireable.

You also tell about geeks who were fedoras. However, nowhere do you provide a credible link between the two except for those people who link them solely for the purpose of picking on the geeks wearing these fedoras – who are, tautologically, not unbiased sources.
We could as well say that they’re wearing the hats because it was an era when a man could take a tommy gun and shoot all who cross them. Or an era when (practically) every guy was a former soldier (we -are- talking interwar period here). Or, more closely related to the theme, because they wish for a time when male fashion was so strict and uniform that all men wore very similar clothing at most times, because it would provide a form of brotherhood. Or maybe a time when notorious criminals could walk the streets, live in luxury and style, and still maintain some sort of code of honour. Or twenty thousand other things.
If anything, ‘when a doll was just a doll’ is one of the worst possibilities available: the Roaring Twenties started with women’s right to vote and included some of the greatest progress in male and female equality. A doll was -not- just a doll in the era of fedoras.

Finally, let’s take a look at your complaints about the idea of the ‘friend zone’. If you think being a geek, fedora-wearing or otherwise, makes people any more or less subject to the phenomenon, I’m afraid I’ll have to prove you wrong. With that greatest of all things, SCIENCE, I can illustrate that it is a general phenomenon among men, without making a qualitative judgement:
http://www.suntimes.com/lifestyles/health/12452915-423/sexual-tension-simmers-in-many-male-female-friendships.html

So to sum up:
1. Your point could have been made by a stereotypical villain.
2. You provide no credible connection between fedoras and any attitude towards women.
3. Your suggested reasons for wearing a fedora are factually disprovable, with many better alternatives available.
4. The attitudes you try to shove into the hands of this arbitrary group of people are, in fact, very broad and general.

That some young dudes look like they are playing bad dress up games in ill chosen and ill fitting attire doesn’t take anything away from that.

We’ve reached the point in society where our everyday wear for women is gender-neutral OR fem. I can (as a cis-het-woman) wear skirts or jeans and a tee-shirt without anyone batting an eye.  (If they do, it’s because I’m a “fashion disaster” not because “women don’t wear that.”)  Traditionally women’s clothing has not become gender-neutral for the most part.  And most average menswear doesn’t strive to be fashion, until you get to more formal stuff.  And we live in a world where cleanly passing as male or female is still very important.  As a cis-woman, I can get away with wearing something that comes off as “neutral,” as long as I still read as female.  A man wearing something fem, would get harassed for it.  Seeming like you’re trying to pass (and not succeeding) can get you harassed or killed.  

So for a (cis or trans) man (or genderfluid individual) to create fashion identity that is distinctly masculine, it’s natural to reach for the few things that are still associated with masculinity, either because they’ve fallen out of general fashion (hats) or because they’re still associated that way (suits and ties).  Or, in the case of a cis-male friend with really odd taste — straw fedora & hawaiian shirts.  And there are a myriad of reasons to want to do so. 

We treat fashion like it’s a “women’s” thing.  Or women and gay men.  Because it’s okay for gay men to be a little fem.  But all of this bashing of the fedora bothers me in part because of these gender issues.  Even as a fedora is a male fashion, because it’s no longer standard fashion, it falls under an individual choosing an interest in style/fashion.  And somehow straight men “aren’t supposed to” be interested in that.  If they want to look good, they’re supposed to ask their girlfriend or wife or female friend to help, because clearly men “can’t” do such a thing on their own.  And I have no problem with men who aren’t interested in style and fashion.  Just as I have no problem with women who have no interest in it.  (Day-to-day, I’m usually one of them.  Until I feel like “presenting” in a particular way.)