Why should a font be treated like a suit? Why not a car, or a house, or another infinitely reproducible digital good? I don't see why you chose that analogy except to set the price expectation at a certain level.
Both fonts and suits are about fashion, and not simply the marginal cost of the goods that go into their production. Clothing fashions could also be made drastically cheaper were it not unlawful to counterfeit them.
Moreover, like an expensive suit (note: I don't own one of those), there is little intrinsic utility in a premium font; it's practically the definition of a digital luxury. It can thus be priced as a Veblen good --- which it in effect is, to its real market (publications, agencies).
And they link to a law paper, "The Piracy Paradox: Innovation and Intellectual Property in Fashion Design" (http://papers.ssrn.com/sol3/papers.cfm?abstract_id=878401) by Kal Raustiala and Christopher Jon Sprigman that says: "Yet a significant empirical anomaly exists: the global fashion industry, which produces a huge variety of creative goods without strong IP protection. Copying is rampant as the orthodox account would predict."
Perhaps what you mean is that you can't claim that a knock-off is from one of the big names in fashion? Because it looks like people copy the designs frequently. Fashion, however, is partly about status, and people attribute status to brands. So even though if a design is similar, people may not value it as high simply because it doesn't have the "right" brand on it.
Moreover, like an expensive suit (note: I don't own one of those), there is little intrinsic utility in a premium font
I actually agree with your point about "okay, so buy two good fonts instead of dozens of crappy ones' -- but I disagree there is little intrinsic utility in a high-quality 'premium' font.
A better font will make the work that uses it more readable and intelligible. It adds _utility_, not just beauty, to the text that uses it.
I'm inclined to believe that because I am a bit of a font nerd, but I don't think it's actually true that text is truly more readable for having spent $99 extra on a premium font for it.
Well, the first question is if a better font text more readable.
The next question is how you identify a better font, and if most $99 fonts are better than most free fonts or not. Certainly there are going to be some crappy $99 fonts, and perhaps a couple good free fonts, sure, the price isn't a guarantee.
I don't know how true that is. There are a lot of things in expensive fonts that provide intrinsic quality: more character sets (greek and cryllic for example), openType features like conditional ligatures, more kerning pairs, extra weights, small caps, hinting, etc.
I do not subscribe to the premise that fonts hold a greater value because they are about 'fashion' and are based on more than just their production value.
App store games, music, etc. are vastly cheaper and hold more than their explicit production value. They provide entertainment, and to an extent, even an artform.
If you have dozen of cars or dozens of houses, I would think you are being just as excessive and profligate as tptacek thinks you would be with dozens of fonts. :)
