The first modern calligrapher to create illustrated envelopes was Francis Courtney (1867–1952). Back in 1908, Courtney sent a series of wonderful envelopes to his friend and colleague, William C. Henning, who was at that time an associate editor of The American Penman (A. N. Palmer’s magazine). Here’s a picture of one of them:

Courtney was a great master of formal calligraphy, in many styles — but his work could also be delightfully strange, casual, and even illegible, when this suited his purpose. (Courtney was way ahead of his time, in this regard.)
Several more examples of these decorated envelopes, all from the year 1908, and many more illustrations of Courtney’s amazing work, can be found in this book: An Elegant Hand: The Golden Age of American Penmanship & Calligraphy.
Today the art of illustrated envelopes is thriving! There’s even an international contest devoted to this art form. Click on winners’ names at bottom of that page, to see some beautiful examples.


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