My favorite new "old fashioned" font is Reinstaedt, designed by Andreas Stötzner. This formal-yet-sketchy face has four slightly different different styles, along with a matching font full of ornaments. But most interestingly, it also has a fill font that you can use to create a different-colored background behind any of the other font styles. For more information on how to do that, see my Zebra font column. You can purchase each style separately. Prices range from $10 to $40. The full family of seven costs $98.
For an absolutely beautiful set of snowflakes, see Deniart’s Snow Crystals font. This charming set of 62 unique symbols includes traditional snow crystals as well as an assortment of bonus characters such as starbursts and holiday accents. Thoughtfully, the package includes a PDF guide to all the characters, to make it easier to find the one you want. Price is $15.
For a unique take on winter precipitation, have a look at Snowflake, a new font by Jessica Hische. Snowflake is based on the look of cut paper snowflakes. It also resembles Mexican papel picado—so you can use it for summer events too. This $59 font includes a full set of accented characters and a few ornaments. There's also a separate, complementary ornaments font for $20.
To go off the deep end of whimsy, try LDJ Doodaddles, by Lettering Delights. This $3 font has stars hanging from its characters, lending a distinctively party-like attitude to invitations or any other messages you use it for.
Sets of holiday dingbats are available in any style you can think of. My favorite this year is LiebeChristmas, by Ulrike Wilhelm. This $15 font contains more than 100 whimsical drawings of Santas, Rudolphs, gifts, treats, and—my favorite—gingerbread men. Individual images let you print distinctive cards and gift tags for different friends and family members
TXT Santa Font
TXT Santa Font, from Lettering Delights, is a weathered, vintage style font. It works well when set in upper and lowercase, but also when set in all caps style. That's unusual for this sort of font , but very pleasing. Plus, it's an easy-on-the-wallet $3!
If your tastes tend toward the old-fashioned, Font Marketplace has an assortment of perfectly lovely script and other winter-inspired fonts for $5 each.