I recommend doing italics first. That is because between these four projects, creating italics will add the most value to your font. A functional font family includes a regular, or roman style, and an italic style. In many cases, italics are mandatory, for setting names of works of art, for example. They are also the best way to emphasize words in text. What about deriving the bold weight, you may ask? Well, bold is much, much less commonly used than italics. A font family does not need a bold weight to be functional, though it can be a selling point. Bold is usually used in contexts where it would also be appropriate to use a completely different typeface (headings, for example). The bold weight is also much more straightforward though tedious to design. It is also much easier to embolden both a roman and an italic typeface to create the bold and the bold italic than to italicize both a regular and a bold font to make the italic and bold italic. That is why I like designing italics before bold.
What are italics?
Italics are much more different from the regular style than the bold style is. In serif type, it is possible to machine-produce a passable, though ugly, bold font given a regular font, since emboldening is a relatively straightforward and mechanical operation. Indeed, dozens of weights can be automatically interpolated (with quite good results) from just three base fonts (extra-light, regular, and black). However it is impossible for a computer to automatically produce the italic style of a serif font (something the opposite is true in sans serif type, where the “italic” is very close to a machine slanted version of the original, and the different weights are given much more consideration). That is because the serif italic letterforms themselves are drastically different from the roman letterforms. Italic letterforms are much closer to calligraphy than roman letterforms are. In fact, the italic hand is one of the most natural styles of calligraphy. This is evident in the strokes of the italic letterforms, which are more cursive than those of roman letterforms.
|(Somewhat messy) italic calligraphy of some lyrics from How You Get The Girl, in Taylor Swift’s 1989. While handwritten, this calligraphy is essentially the same as italic type. Compare this with the Proforma Italic sample below.|
For comparison, here is a sample of the italics from the Proforma font (grouped by letter shape):
The letterforms are much more free-flowing and give a completely different texture than the roman style does. Here are some important differences.