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1. Choose Format>Style and select Heading 1. (If you’re not already using Heading 1 in your document, change the List: dropdown to All styles)
2. Click on the Modify button.
3. Change the Style based on: dropdown from Normal to (no style) at the top of the list, then click on OK. While the dialog is open, choose Format>Paragraph and set the Left indent to 0 and the Special indent to (none). If there is any indenting, these will be set later. If you had already formatted Heading 1, you may need to make some changes after detaching it from Normal.
4. Select Heading 2, click on Modify and change Style based on: to Heading 1. OK out.
5. Repeat step 3 for each built-in Heading style, for as many levels of outline numbering as you require. Each style should be based on the one before.

1. In the Paragraph section of the Home tab, choose Multilevel List>Define New List Style. Avoid starting from Numbered List, that is not reliable.
   

   

2. In the Define New List Style dialog, give your style a plural name like Headings or Numberings, since this will apply to several styles.
3. Click on the Format button and choose Numbering.





4. Now the Bullets and Numbering dialog opens, an extra step that doesn’t happen in Word for Windows. If you need straightforward legal-style numbering, there is a preset shown in the window that can save you many of the steps in the routine outlined below. Click on the Customize button.
   

1. Finally we get to the Customize Outline Numbered List dialog. Once this dialog is open, we will leave it open until all levels are set up. Start by clicking on the dialog expander button to see all the options (circled in red):
   

   

   

2. Start by selecting 1 in the Level list.
3. Next, we attach the paragraph style to the list style. Select Heading 1 in the Link level to style dropdown:
   

   

   

4. Now set the numbering for the style. In the Number format: (Word 2011) or Enter formatting for number: (Word 2016/2019) field, delete any content displayed. If the first outline numbering level starts with text, like Chapter 1 or Section 1, type in the text and a space.
5. Using the Number style: (Word 2011) or Number style for this level: (Word 2016/2019) dropdown, choose the number appearance. Outline Numbering in Word for OS X has a quirk: the Level 1 choice is already displayed, even if no number appears in the Enter formatting for number: box. Just click on the dropdown and re-select the Level 1 that already appears selected and Word will do the right thing. A number appears in the Number format: or Enter formatting for number: field.
6. Add any punctuation or symbol that is to follow the number.
7. Set the Number position and Text position. Both numbers are the distance from the left margin. Left alignment for numbers is most common, but Roman numerals can look better right-aligned, since their width varies more. Normally the tab and indent are set for the same amount. The tab controls the position of the first line and the indent all the lines in the paragraph after that.

Doing the rest of the levels involves repetitive steps that get a little longer with each level. Here are the steps for level 2:

1. Select 2 from the Level list.
2. Choose Heading 2 from the Link level to style: dropdown.
3. Delete the contents of Number Format: (Word 2011) or Enter formatting for number: (Word 2016/2019).
4. Set Previous level number: (Word 2011) or Include level from: (Word 2016/2019) to Level 1.
5. Type a period.
6. Click on the Number style: (Word 2011) or Number style for this level: (Word 2016/2019) dropdown and choose 1,2,3, ….
7. Set the Number position and Text position.

So far, so good. Now let’s do level 3:

1. Select 3 from the Level list.
2. Choose Heading 3 from the Link level to style: dropdown.
3. Delete the contents of Number Format: or Enter formatting for number:.
4. Set Previous level number: or Include level from: to Level 1.
5. Type a period.
6. Set Previous level number: or Include level from: to Level 2.
7. Type a period.
8. Click on the Number style: or Number style for this level: dropdown and choose 1,2,3, ….
9. Set the Number position and Text position.

Steps for Level 4:

1. Select 4 from the Level list.
2. Choose Heading 4 from the Link level to style: dropdown.
3. Delete the contents of Number Format: or Enter formatting for number:.
4. Set Previous level number: or Include level from: to Level 1.
5. Type a period.
6. Set Previous level number: or Include level from: to Level 2.
7. Type a period.
8. Set Previous level number: or Include level from: to Level 3.
9. Type a period.
10. Click on the Number style: or Number style for this level: dropdown and choose 1,2,3, ….
11. Set the Number position and Text position.

Are you seeing the pattern? Each additional level repeats the previous steps and adds 2 new steps. By the time you get to level 9, you’ll have set the previous level and typed a period 8 times before setting the last number!

Like every good designer, you’ll probably want to tweak these styles later. For paragraph styling, like the amount of space before or after, you can simply modify the paragraph parameters. That’s easy. But anything to do with the numbering or its positioning relative to the paragraph should be done in the Outline Numbering dialog. Unfortunately, both Word 2011 and 2016 have a completely non-intuitive method for getting a list style into editing mode.

1. In the Quick Style Gallery, right-click on Heading 1 and choose Modify Style.
2. Click on the Format button and choose Numbering. The Bullets and Numbering dialog opens to the List Styles tab, where you can’t Add, Modify or Delete anything: the buttons are permanently disabled. Serious bug!
   

   

3. Click on the Outline Numbered tab. None is highlighted, which is not helpful. Examine the tiles carefully, you have to choose the correct one. Since you have linked styles to levels, the tile you are looking for will show the first 3 of those style names, but then several other tiles will also show the heading names as well.
4. Click on it the most likely suspect and see if the Reset button becomes enabled. That only happens with user-created list styles, so that’s an indication of the correct tile.
5. Now click on the Customize button. This will only work if you are editing the outline numbering on the same installation of Word on which you originally created it. Open in a different installation or version and the Bullets and Numbering tiles do not show your custom list.
6. Edit the numbering, then exit when you are finished. Instead of editing your named List Style, Word has created a new list style autonamed Current List1.

If you’re using a different installation of the program than what you created the list on, you can’t even use the Outline Numbered tab. All the tiles will display the stock numberings. Instead of editing your list style, you must start all over and get it right in one editing pass.

Here are the final results for an outline numbered style as created in Word 2011. These shots are from the same dialog, only the Level number has been changed.

You can use Brandwares’ expertise to set up your outline numbering. Contact me at production@brandwares.com for an estimate.