How to pick a font

The first step in breaking away from the tyranny of Times New Roman is simply to pick another font. “But I can’t tell the difference between fonts. How will I ever pick a new one?” Don’t panic. Can you tell the difference between these fonts? If yes, then you can do this. Trust me.

  1. Make a document for testing fonts. Take two recent documents you’ve made—perhaps a short motion and a letter to client—that have a variety of font styles in them (bold, italic, etc.) and use a mix of characters (alphabetic, numerical, etc.) Print out these documents and set them aside as your “control” set.
  2. Review the fonts on your system. Purists may hate me for recommending this, but hey. While you shouldn’t use the operating system fonts, most software packages these days (including Word and WordPerfect) come with a giant pile of fonts that get installed with the software. Many of them are dreck, but some are good. So if you haven’t recently, take a moment to go through your font menu and see what’s lurking there. For any font that seems reasonably promising, apply it to all the text in your test document and print out a set (but don’t make any other tweaks or adjustments).
  3. Compare the new documents to your control set. Now you have a set of test documents showing the different fonts. At least a few will be obviously wrong, like the shade of orange that looked great on the paint chip but not so great on your whole dining room. Throw those out immediately. After that, work it down to maybe three or four samples that you like.
  4. Use each one for a week. Resist the urge after step 3 to pick the font you like best and go with it. That’s risky, because sometimes a font you like on Monday gets tiresome by Wednesday. If you commit to using it for a week, you’re more likely to discover whether you have the potential for a long-term relationship. Once you send that memo to everyone in the office saying that “From now on, Olde Noisome Roman is our official text font”, it’s harder to unwind.
  5. Pick the one you like best. There is no right answer. If you’ve compared a number of options and given them a chance to sink in, you’ve done your due diligence. But if you still don’t like any of them, keep reading.
  6. Find a font you like and try that. Find a book or magazine whose font you like. (Not a newspaper—newspaper fonts are optimized for setting dense blocks of text and don’t look so great in normal legal documents.) Scan the page and upload it to WhatTheFont. WhatTheFont is a terrific free service from MyFonts that will analyze your sample and automatically figure out what font it is.
  7. Buy the font and try it out. Buy it, install it, apply it to your test document. If you don’t like it, repeat step 6. OK, you’ll be spending a little money, but it will be worth it to find that special font.
  8. Can’t I just go to a font website and start browsing around? Sure, but it’s not a great idea. There are thousands of fonts available these days and honestly, even I can’t tell the difference between a lot of them. If you’re not a professional designer, it’s more likely you’ll only come away bewildered by choices. But if you are undaunted, here are some sites that carry a wide selection of text fonts:
    Adobe Fonts
    Font Bureau
    FontShop: the online font superstore. Prepare to be overwhelmed.
    Lanston Type Company
    Linotype
    MyFonts
    Monotype / Fonts.com: another superstore.
  9. Arrrgh!! Can’t you just tell me some good fonts? Of course—I’m always happy to impose my taste on others.