Edit: After a second reading, I think I've cracked it. The author is describing Karp as currently immature, but gradually developing into CEO material. So the descriptions separate each aspect of his appearance and personality into "immature", "developing", or "CEO-like".
If you look for it you can easily identify how much emphasis people put on their outfit. So our author is somewhat focused on that, and a number of my east coast friends have been trained by social cues what "is" and "is not" acceptable dress, which they follow or don't in equal measure. It is one of the more observable culture differences in the US.
Does that agree with your experience?
I'm careful not to assign 'caring' or 'not caring' because it is that the attribute of caring is more evenly distributed, its more about awareness for me.
I'd say that the fashion corridor runs from New York (epicenter) down the eastern seaboard.
Paul Graham's "Messages cities send" piece is a pretty interesting reflection on this:
It's cool. 5th largest city in the country and everything, but you know, whatever.
He was listing the cities in the Northeast corridor.
But thanks for the clarification regarding the attention paid.
The choice to go into greater detail regarding appearances, as opposed to making some sort of sweeping statement about "hipsters" or "Brooklyn-folk", came across as mostly unnecessary.
The writer's jealousy just shows through in this. "The enormous features that read so well in photos looked cartoonish in person: Chiclet teeth, rubbery grin, duck-feathery hair."
Yeah, if it had been a slam poet, how much are we betting the writer would have said something like "Wavy hair, dreamy eyes, and delicate-boned face"?
And then, of course, lots of publications have deeply ingrained political (even social) leanings that they more or less openly display; if you want to get a job there, you better share the mindset.
Alternately, let me put it this way. Is there anyone on HN who has a job at NYMag?
The reasons behind why this is a popular style of portrayal may very well be as you say, but it could very well be just a deep seated need to mark those who have vast differences in ability as being of a very different social or behavioural group. This need to be different could stem from jealousy, and a general uneasyness about their own life acheivements.
After all if the tremendously successful aren't different, and are instead just like us, then how are they so much more successful? Why are aren't we all successful? That's an uneasy thought, so humans may want to dismiss it by saying "They must just be 'different.'"
Either way, it is ridiculous that tech 'journalists' feel that they have open license to mock the physical appearance of males in the technology industry like this, because, face it, who's going to stand up on their behalf? It's a thin line between general mud-slinging and actively malicious intentions . The classroom bully also sometimes does it "just for fun", he doesn't have "actively malicious intentions".
On the other hand imagine the outcry if an article had described Marissa Mayer in this photo (http://i.huffpost.com/gen/881509/thumbs/r-MARISSA-MAYER-INTE...) as "having a cartoonish smile, with stringy blond hair, BO, and a surprising number of wrinkles." (note: NOT something I intend to be taken seriously, just an example of generally saying horrible things about a person). People would have been up in arms about "objectifying women in the tech industry and criticizing their looks instead of concentrating on their successes."
Half the Melissa Mayer pieces I read, spend a great deal o the article talking about her fashion sense. No only do people not mind it seems like it's a prerequisite for writing an article about her.