Generate mailing labels with OutlookWell the Holidays are upon us and we need to generate mailing labels  to address this years holiday cards. So once again I turn to Microsoft Outlook to handle the task. Sadly, Microsoft does not make this the easiest task to perform. All of our relatives and friends are indexed in Outlook contacts and it would be time consuming to re-type each one into Microsoft Word or Excel in order to generate labels. Not to mention unproductive trying to maintain more than one mailing list.  Nonetheless, if you follow the procedures below you can quickly print your mailing labels and make your holiday season a little less stressful. Hopefully, the time you save will mean an extra hour or two by by a cozy fire with the ones you love.

Requirements: Microsoft Outlook, Microsoft Word, and Friends & Family (aka Contacts)

Note: We used Microsoft Outlook 2007 and Microsoft Word 2007, the procedures maybe slightly different for other versions.


  1. Categorize: Using Outlook, open your contacts and click on Tools > Organize and create a new category to organize your contacts, call it Holidays. Then go through each contact you wish to send a holiday card to, right click on them and select Categorize and select the category Holiday.
  2. Verify Address: Verify each contact has a complete address and that the address is properly formatted with street address on line one and the city, state and zip code on line
    If you are like me and prefer to address your friends and family in different ways depending on if they are a family, a married couple, single or even a child, ie. The Dalton Family or Mr. & Mrs John Dalton or Mr. John Dalton or even Master John Dalton; you will need to create a custom field in Outlook to achieve this. Microsoft Word which you will eventually use to format the labels offers numerous formatting options, however the formatting must be the same for all and will not meet our requirements.
  3. Create A New Field in Outlook to Customize the Name: View > Current View > Customize Current View > click on the Fields button, then select the drop downs User-defined fields in folder and click on the New Field button, name it Full Name 2. Using the Move Up button, move it up just below the field Full Name and close out the windows. You will now see the new column to the right of the Full Name column. Go through each contact and enter the name the way you would like to address them on your mailing label.
  4. View By Category: In the left column of Outlook click on By Category under Current View. This will display all your contacts grouped by Category.
  5. Selecting all Contacts in Holiday Category: Scroll to find the Holiday Category and select all by clicking on the first contact then holding down the Shift key, scrolling to the last contact and clicking on it. Now all the contacts in the Holiday category are selected.
  6. Export List to Word: Once all desired contacts are selected in Outlook, click on Tools > Mail Merge > Click the radio button labeled Only selected contacts and select the Merge options Document Type drop down Mailing Labels and click OK
    Microsoft Outlook Mail Merge
    Microsoft Office Word will automatically open. You will see the following pop up window in Word, click OK
  7. Microsoft Word NotificationSelect Your Label Type: The Mail Merge Helper window should automatically appear. Next to #1 Main Document click the Setup button and select your mailing label type. We use Avery US Letter 5160 and click OK. Then click on the Close button, to close the window.Microsoft Word Mail Merge
  8. Run Mail Merge Wizard: Click on the Mailings tab and click on the Start Mail Merge Icon, and select Step by Step Mail Merge Wizard. (Note: you may have to click the icon twice for the drop down menu to appear)Word Mail Merge WizardTo the right of your document should appear a column, make sure the radio button Use an existing list is selected and click the link that reads Edit recipient list. It may take 5 to 30 seconds for your contact list to appear. If you would like to remove a contact you can do so in this screen, otherwise click OK. You will now see the placeholder <<Next Record>> in your document in all position except the first.

    Microsoft Word Mailing Label placeholdersIn the lower right corner of your screen, under Step 3 of 6 click the Next: Arrange your labels link

  9. Customize the Label Appearance: In the right column, under Arrange your labels, click on the Address block link. The Insert Address Block window will appear, select the first recipient’s name entitled Josh, deselect Insert company name,  then click on the Match Fields button
    Word address blockIn the Match Fields box, the first item will read Nickname, click on the drop down box and change Nickname to Full_Name_2 and click OK.
    word match fieldsThe Preview box will now display the new layout, often it may jump to another setting. Select the first field Josh again and uncheck the Insert company name. Now the preview should appear correctly. You also have the ability to toggle through and preview each name. Click OK to close the window. And in the place of the first label position you will now see <<AddressBlock>>
    To apply this layout to all labels, you must click the Update all labels button under the Replicate labels heading in the right column. You should now have a document that looks like this:
    word labels
  10. mailing labelsPreview Your Labels:
    Now click on the link in the lower right corner of the screen, under Step 4 o f 6 which reads Next: Preview your labels. Your Word document will now display the first page with of your contact labels
  11. Complete the Merge:
    Click on Next: Complete the merge under Step 5 of 6
  12. Print Labels:
    Load the label paper into your printer and print out your labels.

Happy Holidays everyone!