How to Print Mailing Labels

Updated October 3rd, 2020.

UPDATE: Apple’s Address Book app has a new name. It’s now known as “Contacts,” starting in OS 10.8, for consistency with the name used on the iPhone. The label printing works the same way regardless.

(Are you looking for how to print mailing labels from your iPhone or iPad? Here’s my article about that, updated for 2015.)

Printing mailing labels is easy, especially if you’re using Apple’s Address Book. There are plenty of reasons to like the Address Book but the mailing list printing is one of my favorites. Here are some tips for printing beautiful labels with minimal work.

BONUS: a lot of this applies to printing envelopes, so even if you’re not a Mailing Label guy there’s a lot of good stuff in here for you too. Yes, you could stand at the printer and feed envelopes one at a time for your entire Christmas card list, for example.

Here we go.

Step 1: Get your list together. You’ll almost certainly want to print labels for a group of people, not for just one and not for all of them. So, it’s time to make a Group. Here’s a picture.
One way to make a group is to click where the blue arrow is pointing. That gives you an empty untitled group, so you rename it (easy) and then you click on “All Contacts” and one-by-one drag cards into your group. That second part is not so easy– it’s a lot of dragging. Far easier: start in the “All Contacts” group, then click on ONE person that will be part of your group. Then, hold the Command key, and click on the rest of the people who belong in the group. Then, go to the File menu, and choose “New Group from Selection.” It does exactly what the name suggests. Rename the group (double-click on its name) and you are ready for Step 2.

Step 2: Be sure that the addresses in your group are labeled properly. The Home address should have a “Home” label next to it, for example. If the label is wrong click the Edit button and fix it. You’ll be glad of this later.

Step 3: Click on the name of the group, then go to File and Print. It is very important that you click on the name of the group. Otherwise, when you go to print, you won’t be able to print labels for the whole group. Everyone forgets to do it once in a while, even when he knows better.

The Print box looks something like this. First, be sure the Style pop-up (middle right) is set to “Mailing Labels.” Next click the “Layout” button just below that. That’s where you get to choose the the type of label you’ll be using. BIG HINT: use an Avery brand label. The Address Book is ready for any of more than 100 Avery sizes. Here, I’m using Avery 5161 (2 across, ten down– a little more than a penny apiece).

Step 4: Now click on the Label button.

This is where you get to specify what gets printed. Notice the “Addresses” menu. By default, it says “All.” You might think that means “Print a label for all of the people in the list.” What it really means is “Print a label for every address in the list.” So, if a person has a home and a work address, you’ll get two for that person. Unless the people in your group have only one address each the “All” option is not what you want.

When you click on the “All” pop-up you see something like this (I say “something” because you probably don’t have a Texas category, nor a “Primary Mailing” category– those are custom, beyond the scope of this article). The way this list works is, if you choose “home”, you print only the Home addresses. If you choose “work” you only print the Work addresses.

The wild card is the “Distribution List” option. This can be a handy thing but no one knows how it works. It’s worth finding out so read on!

A Distribution List lets you print a Work address for some of the people, and a Home address for others, and an “Other” address for still others, all in one group, all in one shot. It is a lot better than intentionally mis-labeling someone’s Work address as “home” just because the rest of the addresses in the group are Home addresses. So, cancel out of the Print box and choose Edit Distribution List from the Edit menu. Here’s how it looks.

The problem with this box is we’re interested in mailing addresses, and they’re showing us email addresses instead. That’s OK. Just click and change it to Address.

Now you have a box like this.

All you do is click on the address you want to print, when you print this particular contact in this particular group. The address turns bold to indicate you’ve chosen it (see above). You can manage ALL of the Distribution Lists right here in one box– just click on a group, and then work your way down the list of addresses at the right, clicking once on the address you want to use for each person. Important Note: it is perfectly OK to choose to print Joe Smith’s home address when you’re printing from a Friends group, and to print Joe Smith’s work address when you’re printing from your Prospects group. Apple’s Address Book lets you use a different address for each person on a group-by-group basis. The Address Book remembers what you’ve chosen for each group so you don’t have to do the work twice.

In practice it is pretty hard to remember which address you’ve chosen for each person in each group, so you may go back to this Distribution List box a lot. Once you get it right, you can choose that “Distribution List” option in the Print box, to great advantage. Without the Distribution List there’s no way to print some home addresses and some work addresses and some “other” addresses from the same group, all in one shot. So get to know the Distribution List and save yourself a ton of time and trouble.

There’s a lot to the Address Book but none of it is very hard. There’s just a lot. Take it step by step and you’ll be fine. In case you’re wondering, this is about ten zillion times easier than doing it in Word with one of their templates. Don’t even bother.

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