You're mistaken about the design though. It's both funny to make the design so minimalistic, and yet simultaneously a pretty bold assertion of brand power. And since we don't want HN to grow fast, we don't need to send any messages to anyone who doesn't already recognize the shirt.
Communication is hard.
Bob Dylan's "Ballad of a Thin Man" might be appropriate reading here. :)
I 'got' the design because of the description, but if I had seen it randomly on the street, I'm not sure I would have immediately associated it with HN.
Not sure that any of this matters, but the marketing/branding side of me finds the whole color scheme thing an interesting discussion.
Some people will like the shirt and buy it. Some people will not like the shirt, and will not buy and and not make any comment on it. Some people will offer some kind of critique, which is sort of fun but kind of futile (the shirt is made and being sold. It's too late for critique unless you're going to make and sell another batch in future.)
But what to do about the people who don't like the shirt and loudly tell everyone that they don't like the shirt in ways that are not interesting or useful? Do downvotes work for that?
Do you need to give a small group of carefully vetted people a super-downvote button? (This would be based on your knowledge and trust of those people, not on any karma scores). ((I've wanted to start a hoax about the HN secret pages for high karma users. I've resisted because that kind of meta drama can be pretty harmful, and there are other places where it'd be more fun.)
I've experimented quite a bit with it and have some theories about when it works and when it doesn't, but it's still not completely predictable to me.