I don't particularly like my handwriting—neither did my third grade teacher. Maybe that's why I'm attracted to professional fonts that look like handwriting. Or maybe it's because they're just plain awesome.
Fonts that resemble handwriting are as old as the Macintosh itself—the first Macs included Susan Kare's 72-dpi bitmap font Los Angeles, and Apple includes the font Lucida Handwriting in Mac OS X.
Although Lucida Handwriting doesn't look like anyone's handwriting to me, the characters do connect nicely. If you want a font that looks like your own handwriting, you can do that for a very reasonable price—often under $10—online. For example, at YourFonts and Fontifier, you simply download and print a template, fill in the boxes with your handwritten letters, then scan and upload the template. The Website lets you tweak any letters that don't look right, and then it generates a font for you. You can even include your signature as one of the characters.
If you want more control, and are willing to spend $30, have a look at FontLab's SigMaker, which lets you convert your handwritten letters or any other line art into a font, or add new glyphs to an existing font.
But what if, like me, you don't actually like your handwriting? The Web is full of free fonts that are based on someone else's handwriting. I've found several that I like and I use them as if they were my own. Have a look at the handwriting fonts at FreeFonts, FontSpace, and Font Garden, for example. For more, use Google to search for "free handwriting fonts".
For a more professionally produced handwriting font, look to Chank Diesel's Go Font Yourself, volumes 1 and 2. Each collection contains several dozen handwritten fonts by real people.
You can even impersonate a famous artist—the P22 type foundry professionally digitized the handwriting of several prominent artists, including Cezanne, Gaugin, Van Gogh, Frank Lloyd Wright, and even Leonardo da Vinci.
Some fonts make use of the OpenType font format's ability to recognize surrounding letters and substitute different letter shapes (glyphs) based on context. The result is text that looks more natural because different instances of each letter don't look the same. A few good examples are Canada Type's Martie Pro (available from several resellers), MADType's Casino Hand, and P22's remarkable Brass Script Pro.
If your tastes tend toward the handwriting styles you've seen in fancy greeting cards, have a look at Rob Leuschke’s TypeSETit collection. He was formerly a typographer for Hallmark, and has imbued his font designs with the timeless grace he developed while working on their card designs.
For possibly the best examples of professional penmanship, see P22's Zaner Pro, an OpenType font based upon the work of one of the most influential penman in American history — Charles Paxton Zaner. One unique feature is that you can apply swashes to the end of a word by typing the tilde character (~). If you keep pressing the tilde key, you'll cycle through a range of swashes. For some typographic inspiration, download their PDF full of examples of its use.
I believe that every person has at least one good font design inside them. Perhaps the abundance of handwriting fonts supports this belief. Or not… regardless, it can be hugely entertaining to flip through a collection of handwritten fonts and imagine what kind of person was responsible for each one. Plus, you might find one that shows people a better version of you.
[Jay J. Nelson is the editor and publisher of Design Tools Monthly, an executive summary of graphic design news.]