Chapter 1. On the Merits of Letters

Let’s talk just a bit about typography, its history, and its impact on design. From the first written words, letters have been the vehicle through which meaning and knowledge have been conveyed. That job is performed in more than one way: the words the letters form impart meaning, but the shape of the letters themselves can make an important contribution.

First, a Few Terms Explained

While this book isn’t meant as a complete stand-in for a true typography textbook, I’d be remiss if I didn’t explain some of the key terms and concepts before we dive in:

Quite simply, the theory and practice of selecting and setting type for printed or digital matter. In practice, it refers to typeface selection and setting the type for a given piece of content. Typography also ensures that the correct letterforms are used and proper punctuation marks are shown, generally finessing the final output to produce the highest-quality end result.
A specific design of letterforms, numerals, and punctuation that generally includes a complete set of letters, numbers, punctuation, and special characters of a specific weight or variant (such as Regular, Bold, Italic, etc.).
Typeface family
A set of typefaces of a common design that includes a variety of weights and variants, often ranging from Light to Heavy in both standard and italic variants.
Technically, the font is the actual computer file that contains the information to define a single weight and variant of a typeface. For the purposes of this book, we’ll be focusing on the latter part of that definition: using the term to refer to Trade Gothic Regular Italic as opposed to that whole typeface family of Trade Gothic.
The tiny “feet” and other little projections finishing of strokes of letterforms in typefaces such as Times New Roman or Georgia. Also used to refer to any typeface with those characteristics.
A typeface designed without any serifs (i.e., the strokes that comprise the letterform’s end without any sort of projection).
Slab serif
A serif typeface where the serifs themselves are generally the same thickness as the stroke weight of the letters themselves, which lends a somewhat chunkier feel to the typeface. Slab serif faces are often used for headings and display titles.
A term that refers to the ends of the strokes of letterforms. Some typefaces, such as Helvetica, have perfectly horizontal terminals in letterforms such as a lowercase “a” or “c” which tend to make them look more closed. Others have a slightly angled terminal, which can impart a more open feel and can aid legibility, especially at small sizes.

Words Have Meaning, but Letters Have Emotion

Consider the images conjured by the lettering on a stereotypical Chinese restaurant takeout menu, or a poster advertising an old Western movie, or the opening credits to the show M*A*S*H (see Figure 1-1). Or Apple’s “Think different” campaign. Or picture any of the classic IBM ads, with their headlines set in those distinctively exaggerated thick-and-thin stroked letterforms. It’s hard to use Bodoni without that coming to mind, at least in some subconscious way. That’s pretty effective branding when a company can own an entire typeface in our collective consciousness.

Our memory is filled with visual synonyms for brands—often defined by the type as much as the words
Figure 1-1. Our memory is filled with visual synonyms for brands—often defined by the type as much as the words

In design there are a few basic elements with which we have to play: composition, color, texture, shape, image, and type. When considering existing branding, color, style, and usability, why give up the one element that covers the biggest part of the page? Type can be as expressive or as utilitarian as you like, and the impression it makes is magnified by the fact that it’s so often 90% of what you see on the screen or the page (at least in publications and websites). So let’s leave the land of neutrality behind and really dive into our own expressiveness.

Type is wonderfully versatile and can convey far more than simply the content of the words it spells. It can have gender, color, tone, and emotion all its own. Good typography uses this to impart greater meaning. Great typography can elevate and amplify the message even further, creating its own tension, dynamism, and nuance far beyond the words themselves.

Even when the desire is a bit more practical, choice of typeface impacts readability as much as size and contrast. The actual media makes a difference as well. Newsprint, fine books, mobile phones, television screens, and laptops all present type differently—with widely varying degrees of detail. Choose the form of your letters poorly and your message will be lost and your brand forgotten.

Remember to Be Memorable

When nearly all the sites on the Web are using the same few typefaces (let’s face it: the overwhelming majority specify Helvetica or Arial), it’s noticeable when you use something different. Very noticeable. You can instantly change the tone of the page by shifting the headings and body copy into something just a little bit different. And different can mean memorable—and that kind of memorable can translate into more visits, more recommendations and more transactions.[1] When website visitors make judgments about a site’s usability and value based on aesthetics, every decision you make about your design matters. A lot.

Do Good Looks Affect Usability?

You’d be surprised just how much they do. A good place to learn about the topic is this post by Jennifer Chen on, titled “The Impact of Aesthetics on Attitudes Towards Websites.”

Roots, Rhythm, and Rhyme

As with the examples at the beginning of the chapter, we know we associate certain letterforms with topics, places, and times. Those associations can be used to support (or contrast) the message of your design—but you can only do so if you understand and identify those associations. This is where knowing your history—your roots—and doing some research helps unearth details that really enrich your design. Identifying typefaces that have a relationship to your content or client can give a sense of place, evoke a mood or even reference a specific period in history.

I was fortunate to have been in Paris recently with my wife, and one of the things I sought out was one of the old Métropolitain signs for the Paris subway (originally designed by Hector Guimard). That typeface instantly transports you to not just the place, but that period of time, with its distinct relationship to the Art Nouveau style (see Figure 1-2). Interesting ties can be seen in other city transportation systems, like Helvetica in the New York City subway system or Johnston in the London Underground. But a single typeface is not the only consideration. More often than not, you will likely want to pair different typefaces together, and not every combination will sing in the same key.

Metro sign outside the Louvre in Paris
Figure 1-2. Metro sign outside the Louvre in Paris

The pairing of typefaces and their impact on harmony and readability is a tremendously important aspect of design. Using a distinctive typeface in headers is great, but without considering what comes after, one can end up with some fairly odd bedfellows. The aforementioned Métropolitain typeface would look a bit odd sitting atop a few paragraphs of Helvetica or Arial, but Parisine (designed in the late 1990s and now the standard for use in the Paris Métro system) has a clear relationship and historical tie that might make a lot more sense. (Well, setting headlines in Métropolitain might not be the best choice for readability, but that’s not the point here.)

What we want to achieve is a visual harmony that helps the reader flow from one element to the next, so pairing typefaces that have similar characteristics can create some wonderful and unique designs. Of course, you may choose to go in the opposite direction and look for pairings that have greater contrast in styles. There’s no absolute “right way”—but that’s the nature of design. Sometimes rules are meant to be broken, so long as the result feels right.

Adventures in Typeface Pairing

Here’s an experiment you can try at home: when looking for a typeface for body copy to pair with one you’ve selected for headings, look at other typefaces from the same designer. Even when they aren’t designed together, there are often relationships that stand out simply because they were drawn by the same hand. A personal favorite is headings set in Lubalin Graph—a great slab serif—and Avant Garde, the sans-serif that inspired it, for body copy (see Figure 1-3). The harmony created by the similarity in letterforms enforces a rhythm between heading and copy that flows elegantly from one to the other.

Lubalin Graph paired with Avant Garde, both drawn by Herb Lubalin
Figure 1-3. Lubalin Graph paired with Avant Garde, both drawn by Herb Lubalin

When looking for pairings, it can also help to consider x-height (the height of lowercase letters compared to uppercase ones), overall horizontal scale (look at the width of letters set in Helvetica or Arial compared with Verdana: the latter is much wider and rounder), and stroke weight. In a rare bit of foreshadowing, I’ll mention that you would do well to remember this trick when we get to later chapters on fine-tuning your fallback fonts and CSS. All of these characteristics come into play when trying to find balance and harmony in your design.

So what’s the rhyme in your reason? To add to your design and your message, not simply convey it. I appreciate Swiss design, but can’t get behind the philosophy that type’s only job is to convey the meaning of the words it forms. Helvetica (and others, but it’s an easy target) is an extremely clean, clear typeface that does a stellar job of telling you which subway station you are in on the map, but will never convey the sense of place and history in the tile mosaic on the wall of the Canal St. stop. It’s like expecting a two-cheek-kiss in a greeting from a drill instructor.

I don’t presume to be enough of an authority on typography to cover it all, but I feel it’s important to give you the background and reasons why we should dive in and use web fonts now, even though the technology is still relatively young, and there are a fair number of tricks and workarounds necessary to use them well. It’s worth the effort, as your site will stand apart in dramatic fashion when it’s done elegantly and with finesse. Websites aren’t much without text, and since you have to set it in something, you may as well set it well.

The Evolution of Type on the Web

When the graphical web first came about, there was actually no way to specify type at all. It was just something you could set as a preference in your browser. The only way to use a specific typeface on your site was to make a graphic of that word or phrase in an image editor, save it as a GIF or JPEG, and add it with an <img> tag (see Figure 1-4). Given that you had no idea if the rest of the type was going to be set in a serif or sans-serif typeface, it generally meant you had to keep your expectations pretty low. After a few years we saw the introduction of the font attribute added to our vernacular, allowing us to specify a series of fonts that would be called in order, and the first one present in the viewing user’s system would be the one shown. This ushered in the Age of Arial.

Pictures of a thousand words: for years we were forced to make graphics of words (right) rather than use live text (left) if we wanted a particular typeface in our designs
Figure 1-4. Pictures of a thousand words: for years we were forced to make graphics of words (right) rather than use live text (left) if we wanted a particular typeface in our designs

The only significant change here for a few years was the advent of CSS—though all this did was shift the specification of one of the few “web-safe” typeface choices from directly inline in the HTML to a separate style sheet. Microsoft was the first to support the new @font-face method of embedding web fonts for use on our sites, but due to incompatibilities with other browsers and licensing issues with font vendors, it was not successful at the time. Font replacement was the first “real” method for showing type “live” in a typeface other than one of the web-safe ones to come along, but with finicky and complex implementation, font replacement was often of limited use and was ultimately made obsolete by the next big development.

Finally, around 2007, @font-face made its mainstream debut, though font licensing remained a barrier to adoption until 2009, when the first web font service launched. Real typographic options for the Web—the whole Web—had finally arrived.

1990s–2007: The Angry Designer Years

The graphical web was first brought to us in the early ’90s and along with the Mosaic web browser, began to usher in our modern browsing era. While it wasn’t actually the first web browser, Mosaic was the first to support multiple platforms and enable viewing of images, listening to audio, and more. What it did not do was allow the specification of what font should be used to display the text on the page. It was entirely up to what the browser specified or the user preferred.

Our typographic vocabulary from roughly 1995 to 2009. #LeSigh
Figure 1-5. Our typographic vocabulary from roughly 1995 to 2009—sigh

We actually weren’t able to specify any typeface at all until Netscape’s introduction of the <font> tag in 1995 and its later inclusion in the HTML2 standard. As long as a typeface specified with the <font> tag was installed on the user’s system, it would work. This is how we ended up with a list of fonts that were “web safe,” meaning you could reasonably count on their presence on the majority of users’ systems (a sampling of which can be seen in Figure 1-5). Because the new standard was designed with fallback in mind, you could list a series of fonts, and the browser would look through the list and display the content in whichever font was the first one found in that list. While some of the specifics changed, this remained the only “standards-based” approach available to web designers for over a decade.


Remember this bit of foreshadowing: the idea of a list of fonts meant that content would come first, and the specifics of presentation were secondary. We must always remember to put “usable” before “perfect.”

Not ones to leave well enough alone, web designers found their loophole quickly in the form of the GIF. Well, not necessarily a GIF, but when making a graphic of a word to use in a heading or a button, using the background transparency feature of the GIF format let us sit those lovely pixels nicely on our carefully tiled backgrounds. Naturally, during the design process those buttons would change about 37 times, requiring new graphics to be created, carefully exported, and then posted up to the web server for review. Things got even more exciting with the advent of mouseover states, so instead we could make 37 revisions of two graphics for every button and heading. That’s your double rainbow right there. Not content to have that be all we had to worry about, accessibility for nonsighted users and the emerging prominence of search engines and their mysterious “bots” made sure we needed to have alt text for every graphic we so laboriously produced.

Lest I forget, we did have a significant upheaval in the web design industry with the introduction of Cascading Style Sheets (CSS) in 1996, with version 2 in 1998 supporting specifying font-family property. This allowed us to move our list of web-safe fonts from our markup to our style sheet. Remarkable progress. Not that it didn’t bring many benefits, but it did nothing to really help push forward the cause of web typography until the inclusion of @font-face in CSS 2.1 in 2007. Sadly, @font-face would not become practically useful for another couple years.

A Step Sideways: Font-Replacement Techniques

Meanwhile, there were two other significant developments in the world of web-design typography, beginning in 2004. At that time, something called Scalable Inman Flash Replacement (sIFR) was released. Through a combination of Flash, JavaScript, HTML, and CSS, sIFR made it possible to use alternative fonts, which you created as Flash movies emedded on web pages. The displayed text could update dynamically, was still selectable, and overall made the Web a much better-looking neighborhood. However, it could be a bit tricky to set up and was not appropriate for all uses: you couldn’t even really think about using it for body copy, and it was often very difficult to use even for navigation elements. Due to its reliance on Flash and JavaScript, it was clearly not a solution for the long haul, but it did provide the ability to utilize different fonts without running afoul of font vendors’ licensing agreements.

A development a few years later was something called Cufón, which lashed together a generated font file, two rendering engines, and some chewing gum and baling wire (OK, guessing on those last two) to create another way of embedding fonts safely within your page without risking font piracy. Unfortunately the text was rendered nonselectable, so it was useless for nonsighted users or search engines. To its credit, though, it was easier to set up and more stable than sIFR, so it did become fairly widely adopted. Ironically, it came along just as things got a whole lot more interesting for very different reasons, sometime in 2009.

Finally: @font-face

Remember when I mentioned @font-face back in The Evolution of Type on the Web? The reason it sat around unloved except by a few for so long was due to the fact that while it was possible to include a typeface this way, and browsers were starting to support it widely, there were not many typefaces you could legally do this with, and you still needed a number of formats to make it all work. Licensing had always been what held back widespread adoption of web fonts, because there was no good way to prevent those fonts from being downloaded to a user’s computer and then saved by him for use anywhere else. Finally, @font-face delivered a way to embed fonts in your page that browsers could keep from being downloaded, and with the launch of web font services came a way to manage that even better.

Admittedly, this has been a very brief overview. But that’s so we can get to the good stuff.

May 27, 2009: T-Day

This was the launch date for Typekit, a new service that let users pick typefaces and easily add them to their websites with just a line or two of code. Behind that was @font-face and a crafty bit of wizardry that prevented users from saving those fonts to their own systems. More services launched soon after, with Fontdeck,, and WebINK being some of the first. I have to say that, more than any other advance or technology over the past decade, this is the one that put the fun back in web design for me.

Dawn of a New Design Paradigm

Alas, there is, of course, still more to this saga. We’re not quite out of the woods just yet. So far we’ve been chatting primarily about desktop browsing—but many sites are reporting 15, 20, even 30% or more of their traffic coming from mobile devices (and one of my own client’s sites routinely spikes to over 50% mobile traffic during high-traffic periods). In truth, the global trend is for the majority of traffic on the web to tip in favor of mobile within the next year. According to StatCounter, in just the past year global web traffic from mobile devices has increased over 50% (see a few examples in Figure 1-6).

Global web traffic from mobile devices, with some data by continent, as reported by[Mashable in August 2013]
Figure 1-6. Global web traffic from mobile devices, with some data by continent as reported by Mashable in August 2013

So what about mobile devices? Well, there are over 50 typeface families available on current iOS devices, with some really nice choices. But we’re still effectively stuck with the “lowest common denominator” choices if we want to be really consistent. And then there’s Android: one of the most prevalent smartphone operating systems out there comes with—wait for it—three fonts. Well, actually four, as of the most recent release, Android 4.4. Cue wails of despair and gnashing of teeth. Clearly there is a need for a better solution to provide any sort of consistency and distinction across devices, platforms, and browsers.

Even though browser support is there for @font-face, font formats remain an issue. Thankfully the formats are available and we can safely and reliably serve our designs as intended to millions of mobile devices, as well.

Font Format Finagling: Who Shows What and Where

While adoption of @font-face was a big deal, there were and are still some significant technical issues with which to contend. First and foremost are file formats: in order to support the fullest range of browsers, OSes, and devices, one must support no fewer than four different file formats for every variant of every typeface! Only recently has a single format emerged as an agreed-upon standard for the future (I’ll get to which one this is in a moment). It leverages elements of HTML5 and CSS3 to provide reasonable protection for font vendors, while evolving into a format and standard that can work and be supported across all devices, platforms, and operating systems (well, eventually—as of April 2014 about 77% of devices accessing the Web support it). However, with access to all of the file formats, fonts added with @font-face are viewable on over 90% of devices on the Web (when tablets and other mobile devices are considered alongside full-fledged computers, vendors such as Typekit and believe the number to be closer to 98%) (see Figure 1-7).

Browser support for +@font-face+ as of May, 2014, from
Figure 1-7. Browser support for @font-face as of May, 2014 from

Let’s dig a bit deeper into the issue of file formats. You’ll have to bear with me just a little bit; this is going to get confusing. One of the most common desktop formats for fonts now is TrueType, although that is being supplanted by OpenType. While TrueType originated at Microsoft, Internet Explorer (IE) is just about the only browser that doesn’t support it for use on the Web (though partial support came around with IE 9). If you want to support earlier versions of IE, you need to use the EOT (Embedded Open Type) format, but don’t expect that to work anywhere else. That’s two. If you want to support earlier versions of Safari (both desktop and mobile), SVG’s your choice (that’s Scalable Vector Graphics). That’s format number three. And if you want to go with the “now just about a fully ratified standard” called WOFF (Web Open Font Format), well, that will do in almost all current browsers (finally including Android, as of the most recent 4.4 release). And just to be clear: none of it works in Opera Mini.


Opera Mini is the only modern browser that does not support @font-face. It’s designed to be ruthlessly efficient with bandwidth and hardware resources, which is why it’s used on many of the devices deployed in the fastest-growing markets in the world (which are also some of the most bandwidth-constrained). Asia, Africa, and India see significantly higher percentages of mobile traffic on Opera Mini than almost all other browsers. Bit of a bummer that it doesn’t support nicer type.

Why all the formats? Why indeed. TrueType and its successor, OpenType, are the de facto standard on the desktop these days. OpenType supports all sorts of typographic goodness—such as full Unicode support for more than 65,000 glyphs, ligatures (think nicer glyphs for double characters like ff, as seen in Figure 1-8), and cross-platform font files—so there is no longer a need for separate Mac, Windows, and Unix file formats. What is lacking is any kind of protection native to the file format to limit use on the Web, like precluding a font file from being served from one domain and included for display on another. To counter that limitation, Microsoft came out with the EOT format as far back as 1996. However, IE was the only browser to ever support it.

Examples of ligatures (standard characters to the left, ligature glyphs to the right in each pair)
Figure 1-8. Examples of ligatures (standard characters to the left, ligature glyphs to the right in each pair)

SVG is the third format, and while it is supported on a number of browsers, the only real reason we are discussing it is that prior to iOS 4.2, it was the only format supported on the iPhone. While that changed at the beginning of 2011, it’s still a bit early to forget SVG entirely.[2]

Finally, there’s WOFF. WOFF is the only font format to reach Recommendation status with the W3C, and it should be come an official standard soon. Technically, WOFF is essentially a wrapper for TrueType or OpenType fonts that adds a significant amount of compression (up to 40%), making it better suited for web use than other formats. As of this writing, more than 77% of devices on the Web can handle WOFF fonts, but there’s still a ways to go before support can be considered universal and other formats can be dropped.

And So the Stage Is Set

So what does this mean for you, the web designer or developer tasked with adding this support? Well, if you are hosting the fonts yourself, it means you need all four formats for every weight and style you intend to use on your site. This is the only way to be sure your web fonts will be seen on all the devices used to visit your site (at least the ones that support @font-face).

Of course, it wouldn’t be the Web if there weren’t a catch. Just because a particular browser and OS supports web fonts, it doesn’t mean it supports them well. Shockingly, the primary cause for this caveat involves Windows—Windows XP in particular—wherein there debuted a new font-smoothing technology called ClearType. I won’t delve too deeply yet into just how much this may vex you, but suffice to say it will likely cause you some angst in the short term. At least there is a brighter shade of gloom on the horizon where font rendering in Windows is concerned: Windows 7+ and IE9+ handle web fonts together quite nicely. But let’s look at the whole process of how fonts show up on our screens in the first place.

[1] As opposed to memorable like, “Hey, remember that legal services site we saw that used Comic Sans for their headings?”

[2] As of June 2014, usage of those early versions of iOS seems to have dropped to about 1% of iOS devices globally, according to, so it may well not be an issue for your user base.

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