We want to automate the printing of envelopes for contacts. That appears, though, to be non-trivial with QuickBooks, Word, and Outlook.com. So, here is a manual process with MS Word 2013.

1. Open a blank document in Word 2013.
2. Click the Mailings tab, choose Envelopes.
3. Add a delivery address and return address.
4. Click Options.
5. Choose the envelope size (e.g. DL (110 x 220 mm).
6. View the printing options without changing them, to learn how to orient the envelope.
7. Load the envelope into the printer.
8. Click the Print button.

Example (note: I am mailing to myself.)

See

http://office.microsoft.com/en-us/word-help/print-an-envelope-HA102809671.aspx