They aren't out of touch, they understand the culture. People here want Hacker News to feel like the last thirty years of the web didn't happen. They don't want Hacker News to be modern, least of all to be like other forums. They want the Bohemian indulgence of 90's era web ugliness with complete disregard for standards, and the ascetic purity of painfully minimalist UX that appeals to their contrarian, anti-modern sensibilities.
The design is based directly on the design of several (what we now call) 'Web 2.0' sites so the idea it's a sop to the retro-hipster sensibilities of 90's-longing users itself feels like a bit of an overwrought personal indulgence.
“So the most important thing a community site can do is attract the kind of people it wants. A site trying to be as big as possible wants to attract everyone. But a site aiming at a particular subset of users has to attract just those—and just as importantly, repel everyone else. I've made a conscious effort to do this on HN. The graphic design is as plain as possible, and the site rules discourage dramatic link titles. The goal is that the only thing to interest someone arriving at HN for the first time should be the ideas expressed there”
I mean, you only have to read literally any thread on HN's design and features, or any of the nigh-weekly threads complaining about the modern web and its complexity, how commodification and capitalism have ruined its creativity and quirkiness, or how javascript exists, to see those sensibilities are alive and well and strongly culturally correlated to the layout of this site and the perception (somewhat inaccurate) that it exists frozen in amber.
None of this says 'ignore standards and the web of the last 30 years'. Some of this stuff was, again, literal web 2.0 shit. Yes, sure, that line of thinking exists here culturally but even its origin is a decade (i.e. a millennium, in web time) off from your original bit of hyperbole.
