How to Print Envelopes and Mailing Labels on Your Mac

When most users think of printing envelopes and mailing labels using their computer, images of custom software and Microsoft Word plugins frequently come to mind. But if you’re using OS X, you can quickly print basic envelopes, labels, and mailing lists directly from the Contacts app. Here’s how.
First, launch the Contacts app, which is located in your Dock by default or in the Applications folder on your Mac’s system drive (you can also search for it with Spotlight if you’re having trouble locating it). Next, select one or more contacts (hold down the Command key on your keyboard and click on each desired contact to select multiple contacts at the same time).

With your contact(s) selected, go to File > Print in the OS X menu bar, or use the keyboard shortcut Command-P. This will bring up the Contacts print menu.

On the print menu, use the Style drop-down menu to select envelopes or mailing labels as desired. The Contacts app also lets you print an ordered list of your contacts or an alphabetized pocket address book.

When printing envelopes, you can customize your envelope size on the Layout tab, with dozens of North American and International options from which to choose. The Label tab lets you choose whether or not to print your return address, which the app will automatically pull from your “Me” contact card, select which address (home, work, etc.) to print for your contacts, and customize fonts and colors. You can also add an image, such as your company’s logo, to the return address field.
For mailing labels, you’ll need to choose the size of your label sheet (i.e., “Avery Standard”), and you can then use the Label tab to customize print order, fonts, colors, and any included images.
When you’ve configured your envelopes or mailing labels, make sure the correct paper or label sheet is loaded in your printer and simply click Print to initiate the print job. Third party software like EasyEnvelopes gives you more options when it comes to printing envelopes on your Mac, such as the ability to use USPS barcodes, but if you just need an envelope or two in a pinch, the OS X Contacts app can get the job done.