Addressing an envelope is a design problem that was once confronted daily. It couldn’t have been a more mundane task. Sometimes it was approached with care. More often it was simply done and forgotten. Today one hardly ever has to consider an envelope—except to pitch it in the recycling bin. However, for many years an envelope was an important part of communication and business. Dwiggins, Tschichold, and Zwart wrote about how an envelope should be addressed. Corporate standards manuals showed how it should be done. Subway posters touted the need to address an envelope in a certain way to ensure speedy delivery.

How did (and do) type designers and graphic designers—people who dedicated their lives to letterforms and communication—tackle addressing an envelope? Sometimes beautifully. Sometimes tragically. We've gathered (and are gathering) envelopes addressed and mailed by some of the masters of modern type- and graphic design to show how the greats approached this most ephemeral design problem.