Selecting a typeface with that special something can be really tough. With all the factors that go into a typeface, from aesthetic and historical traits to the various effects of different kinds of serifs, how can you make a good choice? I'm sure there’s no single answer, but there are certainly some techniques that can help you if not to find the perfect typeface, at least to avoid the wrong one.

One quick tip before we get started: don’t get attached. While you may have your list of the usual favorites, each project carries its own needs and goals. Be ready to leave your favorite typeface. If it doesn’t serve your design, it doesn’t serve the reader either.

I would suggest that you consider the following techniques, but don’t take them for granted, be flexible, and use them as references and starting points for your further choices.

One method you can use is word association. Rather than scrolling endlessly through pages of typefaces and thinking, “Is this the right one?”, look at it from a different angle. Ask yourself: “What do I want my design to convey?” Think of words that describe the feelings or moods you’d like to pass on. 

Grab a paper and scribble down any words that come to your mind. You’re brainstorming, so there are no wrong answers, and you can always cross some out later. The important thing is to write as many ideas as you can. After you’ve exhausted that, start sorting similar words together into groups.

For instance, if you want to present the theme of elegance, you may look at typefaces that are slim, symmetric, and elongated. By narrowing your focus to a word or two it will be easier to collect potential typefaces.

The most useful thing you can do when deciding whether to use a typeface is to try it out in a situation as close to the real thing as possible. If you’re making a website, this means testing that typeface in context on an actual web page.

Some typefaces look beautiful when you see them in printed media or in the context of their marketing pages on websites. However, when you work with them in the frame of your own project, you may experience different results.

Typefaces need to be tried and tested in a real setting. There are some online tools that can help you in this phase. For instance, the extension Webtype’s Font Swapper allows you to preview any of their fonts on a given URL.

Once you review some typefaces in context try to answer the following questions:

• Does the typeface have the right feel? Is it good for extended reading? 
• Do the characters in your headline or company name look strange? 
• Does the typeface family have additional styles you can use to shape different parts of your textual content?
• At this point, you may come out with two or three typefaces as starting points for your further work.

Just as we need to find typefaces that are technically appropriate, we also need to ensure our choices are aligned for our aesthetic context. Most of the time, it’s not a matter of finding a perfect typeface, but rather a matter of avoiding inappropriate ones.

How do we find out if a typeface is appropriate or, more likely, inappropriate? The best place to start is to track down information about the typeface itself. Designers will often outline why they created a typeface, where they drew their inspiration from, what they intended the type to be used for, and more. That information will be helpful in your typeface choices.

For instance, if you want to evoke a certain period, you should look for typefaces made during that time. They may not be exactly what you need, but they have characteristics you can identify and use as criteria for your choices.

Consult Fonts In Use - the independent archive of typography that catalogs imagery of typefaces in real settings. The examples are well documented and tagged so you can quickly get information about a specific typeface. This is also a very good place where you can get advice on which typefaces are paired with the ones you’re researching.

A bit of your research and attention to a typeface’s connotations can definitely make your design more cohesive.

Beyond the basic set of Latin alphabet characters, a serious typeface family may include international character sets, multiple numeral sets, small caps, and multiple styles for text, titling, and captions. That can add up to hundreds of individual symbols per style, which means you’re talking about potentially thousands of letterforms in total. That takes a lot of time, expertise, and testing, which you’re less likely to get with free fonts.

Free fonts usually consist of incomplete character sets (missing lowercase characters, or worse, punctuation). They are characterized by less technical or aesthetic cohesion (the typeface feels uneven) and are likely to be highly derived from another font (sometimes due to an unaware designer with good intentions).

Should you completely avoid free fonts? Not at all, but you should be extra cautious. Good fonts cost money because they take a lot of work to become good fonts.

One last way to make choosing type easier is to narrow the field. Create your own lists, keep typefaces that you know well, or that you would like to use. Those typefaces can serve as a springboard for finding new and related options. But you still need to cull the best typefaces for your design goals, which will shift with every job. A great place to start is by referencing something whose design you already enjoy.

If you see a typeface you want to learn more about, you can use a bookmarklet like Fount to reveal its name. You can also upload pictures to WhatTheFont and check further in MyFonts’ extensive type database. 

Or, maybe you’re the kind of person who relies more on recommendations or scours new typeface releases. Sites like I Love Typography cover type releases on a regular basis. Many textbooks and design annuals offer beautiful examples that identify the typefaces used.

Finding designers you like and researching their type palettes can be a great way to build your own library.

I hope that these few tips will introduce you to the creative world of typography, help you choose the right typeface for your next project, and prepare you for the next phase - pairing typefaces together.

Source: Santa Maria J. (2014). On Web Typography. A Book Apart. New York