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Interesting post, but please don't preface submission titles with "Show HN:", especially if it's not some personal project.
This is a fascinating question; which the article completely fails to answer. Besides fluffy common-sense tips like being aware of what message a font sends and not using what was fashionable twenty years ago, the only concrete advice is:

"Serifed type is often used for long copy, like books and magazines. This is because the serifs make the characters more recognizable and the text easy to read in bulk at small sizes. Serif body copy usually pairs well with sans-serif display type. There are mountains of exceptions, but you have to understand the rules before you can effectively break them."

Everyone knows the serif-for-body-text, sans-for-headings "rule". What we need to know is the next step: what are those exceptions, what motivates them, when do they apply? Why specifically do you choose, say, Baskerville over Stone Print?

By not answering any of these questions, the author gives them impression that he doesn't know the answers.

Does anyone? Because articles like this just reinforce the impression that type choice is a religion that its priests make mysterious for their own job-security. I really want to believe that there's a science in there.

Serifed type is often used for long copy, like books and magazines.

Nowadays, this rule doesn't even really apply. How many websites use serif for main copy? Is the BBC less legible than the NYTimes? At small sizes it is not necessarily more legible on screen. There is certainly very little science in choosing fonts; there is more to the world than is dreamt of in science, but a few guidelines might be helpful.

Here's a typical designer's process in choosing a font:

Consider the use - logo, headling or body copy. For headlines you can afford to have personality and be a little less readable, for body copy legibility is the first concern as it is typically smaller and denser.

Consider the medium and size - smaller requires less personality, on screens in particular. In print serif still predominates, particularly on cheap paper, on screen the converse is true and you might have to use larger type if you want to use a serif.

Consider the context - what do people expect? What message are you sending when using this font? Consider things like branding or corporate guidelines - that might limit your choice.

Finally, consider what mood you want to create, what message you want convey, think of a few adjectives which describe your content. Now look for a font which says all that to you when you first see it. Fonts are like clothes for your thoughts, and like clothes, what they say about the person wearing them is a statement of some kind, even if that statement is just: I don't care about appearances (at this point in time, Helvetica/Verdana).

So once you've thought about the above, choosing a font should be fairly simple, and is a matter of browsing through font catalogues available on your device (or google web fonts for example). If you're still stuck, limit your choice to the older ones which are generally considered classics (Gill, Helvetica, Futura, Bodoni, Bembo, Garamond) - using just a few of those would be fine for many uses.

And don't forget the measure and line spacing as this is the most often overlooked and useful way of increasing legibility and impact (defaults are often too tight - e.g. this site has spacing which is far too tight and a measure far too long).

I'm afraid, for most people, typeface choices appear to be artistic choices shaped by the same dynamics music or fashion progresses.

For artistic web sites, the font choice may accompany, reflect, contradict, ridicule or noisify site 'ideas'. So anything is possible.

For business web sites, a structured approach is definitely possible. UX goals must be followed for typeface choices too, bringing together user's behaviour vs site owner's business targets. A careful choice of font parameters such as spacing, thickness, serif/sans serif/monospace, spacing would be possible.

Edit: a link; http://inspirationlab.files.wordpress.com/2010/04/infographi...

I just registered to reply to your post. I am a designer with a couple of decades experience. There are of course design 'rules' but there is just as much intuition and familiarity.

If I can make an analogy, it may help explain the process of choosing typefaces for a project. I really hope this doesn't come across as pretentious nonsense, as anyone can learn about type, but it really is mainly down to experience and a desire to learn:

So let's say your job is to choose the songs that appear on film soundtracks. You need to be aware of the mood, era and style of the film, and choose compositions to match. Now due to the nature of your job, you will be more aware than the average person of music around you - you are constantly conscious of it around you in your day to day life, as well as researching the history of specific songs and tunes, in your own time, purely for pleasure.

So you'll have built up a mental database of knowledge. For a specific film you could include a popular song that many people are aware of, or you could choose something more obscure, but more appropriate. You might choose a selection of songs by the same artist, or tunes from the same record label, or all songs played in the same key. Simply having more knowledge means you have these options.

There could be a set of rules written for choosing music - 'In a tense scene, use this type of tune', and that would be fine, but it really is one of those things where experience over time, and an enthusiasm, is more valuable than just going by the book.

Bringing it back to type, it's a case of knowing about the moods generated by each typeface. From day to day I am constantly aware of the typefaces used on shop signs, TV and film credits, newspapers and posters; but I also know what fonts would have been used in the same circumstances in 1979, or 1962, or 1890 (although not so much on TV then).

So I've probably not done anything at all to dispel your idea of 'priests of a mysterious religion', but I'd personally compare it more to a hobby or pastime, which, if you're lucky, you can get paid to do.

Brilliant analogy Thos - i was an art director and creative director last century and you nailed it. I'd add that good vintage typographical signage goes for ridiculous prices these days because of their evocativeness and balanced design. Graphic design is very analogous to creating music also, and picking appropriate tonal colors...
Thanks, Thos. This is a helpful analogy and goes some way to explaining why designers have such strong (and often incompatible) preferences for one font over another where I don't necessarily see a lot of difference.