In defense of “how it looks”

I personally love craigslist's 1996 academic webpage design: very little divergence from browser default styles, minimal positioning, and "font-family: serif;".

The "design elite" DESPISE craigslist. There was a long stretch a few years ago where prominent dimwits were putting up their total redesigns of craigslist just about weekly. There have been multiple organized design contests based around it!

I don't find craigslist well designed at all. It is terrible at displaying the information in a digestible format. For example, instead of browsing the rent section on craigslist I go to houseingmaps.com

The full quote seems misguided:

And yet: Please show me a product or object hailed by the design elite as Good that doesn’t just so happen to be aesthetically pleasing. (To the design elite, anyway.) “How it looks,” in other words, matters, both to the critics and to the market.

"Critics" and any "design elite" of note are far, far different audiences than the markets which people produce for. Craigslist, Bloomberg, Myspace are, yes, all examples of this.