One thing you could do is taking a piece that you think is good which is set in one (or more) typeface you like and try to reproduce it.

Here are four different and valid ways to study typefaces.

One is, if they are popular, to look at them in many different uses, and see when you think them well and badly used, and try to analyze why they work and don't in the different settings.

A second is to set them, side by side, in the same setting. And then vary them to see which looks best in what setting.

Third, open them up in a font editor, and paste the outlines of one over the other, to see the differences that are responsible for the different looks en masse. Also look at the way the spacing is handled differently.

Fourth, read books on type. Letters of Credit, by Walter Tracy, is a "must read". Another favorite of mine is Fonts and Logos by Doyald Young. There are many others.

If you do these, often, you a certified typomaniac. Welcome to the crowd!

Just practice. Use the same fonts, year after year, until they make sense. Most of the times I typeset something I use H&FJ’s Whitney. I’ve been doing that since 2008. I’ll get the hang of it one day.

Welcome to the dark side.

Since I'm not much of a type user (I just make the stuff) I myself
can't be too helpful in terms of how to leverage particular fonts, but
what I would offer is what might be the single most useful "big secret"
of typefaces: a font's color (meaning weight), spacing and vertical
proportions* are intertwined (which means they have to be balanced**)
and where a font lies on this spectrum determines its ideal point size.

* Mostly the relative size of its x-height.

** This is why -contrary to what some will have you believe- some
fonts are better than others, and some fonts are just plain lousy.

hhp

If you hold them very close to your face and sniff them it may help you understand them better. There are other ways, but it's best to find that out for your self.

While there may not be set pieces, like scored music which may be performed with specific instruments, it’s nonetheless possible to execute the classic layout formats of various genres, in combinations of different typefaces.

But where can you do this with a real purpose?

Why not start a web site at which to carry out your exploration, and document it?

As a type designer, I certainly get to know the types I’m designing (if they’re retail and I’m working from scratch, not commissioned for a specific project which acts as a testing ground), by making specimen banners for MyFonts, and PDF specimen “books”, some with faux specimens of ads, posters, packaging &c. But you would have the advantage of being able to mix several faces in one piece, rather than just use one typeface at a time, which is the norm for type specimens

Emigre has produced specimens which involve combinations of their fonts -- most notably starting with Emigre magazine twenty years ago. And Typotheque has sample layouts, an advanced form of type tester harking back to some of the old Linotype manuals.

The best way is your own way.

Thanks everyone, I really appreciate these comments!

@ricarrdo i've been doing that a bit but having some trouble finding 'examples'. I am still not very good at identifying typefaces. is there a resource somewhere that allows you see examples of one particular typeface in action? For example, how would one best go about finding examples of Requiem (or any other well-known typeface for that matter)??

@William thanks for these tips... but again, same question. What's a good way to find the typeface in different uses???

@dunwich the journey begins... ;)

@hrant deep stuff.. gotta chew on that for awhile!

@terminal i knew i was missing something! ;)

@Nick Shinn.. I actually just started a 365 project where I'm laying out quotations on photos every day for an entire year. I just hit the 30 day mark and I've learned a ton already. One of my goals with this project is to become more adept at typography.

@dez word, i'm getting there hopefully.. :)

>What's a good way to find the typeface in different uses???
In addition to going into book stores, looking at magazines, newspapers, ads, web sites, etc., you can check out http://fontsinuse.com/.

Also in addition to experimenting on your own, you can follow discussions on Typophile. But do check out the work of those posting, and see if you like it, and take that into account in assessing their comments. Also you can ask specific questions about specific faces—that is likely to get more useful responses, I think.

@Godsfingerprints

"I am still not very good at identifying typefaces. is there a resource somewhere that allows you see examples of one particular typeface in action?

I'm not very good at identifying typefaces either, and I work with a wide variety of them every day. Spending my time slipping font after font into the appropriate mental slot never struck me as an effective use of my time.
Quite the opposite, actually, I'd rather not know - easier for me to focus on what the thing IS rather than on what it's called and how it's categorized.

I once learned what a lachrymal was, by accident, and it took me a week of real effort to finally forget. (No joke.)

But if you're interested in how typefaces look and work together inside web pages, I recommend the outfit I'm currently associated with: Konstellations. If fonts in the context of web design are of interest to you, feel free to contact me directly. (And certainly don't consider the subscription price some kind of impenetrable barrier.)

Here's a look at a recent piece.

And +1 to dezcom's comment on this thread.

Richard Fink
Blog: Readable Web
Type Director: Kernest/Konstellations

A nice exercise we did in school:

Print out 5 arbitrary glyphs from a given typeface. Examine these glyphs closely. Then try and draw some of the missing glyphs (without referencing the font file on your computer).

This helps you understand the structure of the typeface, and it's quite fun to see how different (and often awkward) your solution is compared to the original.

Hopefully this will help you understand how the design of the typeface lends itself to certain settings.

And if you have the scratch: go to www.typecamp.org