Apply Styles to Existing Manually Formatted Document

I'd use the solution proposed by Paulsauve, however as stated it does require ONLY the section headings to be 14pt Bold Arial - i.e. Other text may also be converted.

Failing that - if you know that the start of each section has a heading (or that headings are only at the start of each section) then you could use a macro that converts the first paragraph in each section to a heading, this would be quick.

The approach below looks only at the first paragraph in each section.

Sub Headings()

Dim oSect As Section

For Each oSect In ActiveDocument.Sections
If oSect.Range.Paragraphs(1).Range.Font.Size = 14 And oSect.Range.Paragraphs(1).Range.Font.Bold = True And oSect.Range.Paragraphs(1).Range.Font.Name = "Arial" Then

oSect.Range.Paragraphs(1).Range.Style = "Heading 1"

End If
Next oSect

End Sub

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The find and replace worked well at first, but then there were other parts of the document that happen to be 14pt Arial Bold. I'm thinking though, is it possible to maybe use regex to match? The article sections are always formatted like

ARTICLE XX – TEXT

and the sections are always:

X.X

with an optional third digit, like

X.X.X

So something like this:

(ARTICLE) (\\s+) (\\d+) (\\s+) (–) (\\s+) ((?:[a-z][a-z]+)|(\\s+))+ 

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My regex is not strong, so I don't know for sure if that would work.

Thank you!

Actually something more like this for the article numbers:

(ARTICLE)(\s+)(\d+)(\s+)(–)(\s+)((?:[A-Z][A-Z]+)|(\s+))+

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And then something like this for the sections:

(\d+)(\.)(\d+)(?:\.)(?:\d+)(\s+)(.*)

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This works in my regex tester, but it doesn't seem to work in find and replace in Word using wildcards.

I have seen those, Word's wildcard syntax is a little foreign to me. I have actually found that each section has invisible text used for creating a table of contents. Is there a way to use that to populate the navigation pane? Thanks for your help!

When you say invisible text... do you mean field codes,  hidden text,  the mark up codes, or something else?
Sorry for the brevity  using phone.

No problem, I believe it is a field code. Thanks!

The field code basically displays and formats text that has a "heading style". Same thing for navigation panel. Need to put headings in first.

Right, but I would like to populate the navigation pane using that data. Is that possible?

Yes... once the headings are in the document (as Heading Styles) they should automatically appear in the navigation pane...  sorry not sure I understand where your question is coming from

Macro like this will help with applying headings:

Sub UpdateSections()

Dim para As Paragraph
Dim str As String

str = "(ARTICLE )[0-9]( )^=( )<[0-9A-z ]*[^13]"

ActiveDocument.Range.Select
    With Selection.Find
        .Text = str
        .Replacement.Text = ""
        .Forward = True
        .Font.Name = "Arial Narrow"
        .Font.Size = 24
        .MatchWildcards = True
        .Forward = True
        .Replacement.Style = "Heading 1"
        .Execute Replace:=wdReplaceAll
    End With

End Sub

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No Problem, I was just asking if I could use the information in the field code to populate the Navigation Pane. So like adjust heading styles everywhere there is a field code. Sorry if I was being vague!

You can do that via the styles pane, but only once the styles are applied.  Incidently you can also apply styles via the styles pane :-)

Ok, so how would I do that? Is there a way to select all the text that had field codes?

Can be done using vba.  What field types are you targeting? Rclick and show field codes.
Sorry for the brevity - on phone

Back at PC - this might help:

Sub FindFields()

Dim oFld As Field
Dim strHead As String

For Each oFld In ActiveDocument.Fields
If oFld.Type = wdFieldRef Then
' Apply Style based on other conditions?
strHead = InputBox("Enter a heading level for this text" & vbCr & vbCr & oFld.Code.Paragraphs(1).Range.Text)
If strHead = "0" Or strHead = "" Then
Else
oFld.Code.Paragraphs(1).Style = "Heading " & strHead
End If
End If
strHead = 0
Next oFld

End Sub

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Here is an example of the field code. Thanks!

Is the "2" the heading level that you wish to apply?  Is this field in the Table of Contents or elsewhere in the document?

Oh... it will fail if the \L or number is missing

This all looks good. My question changed a bit throughout, so a solution based on this should work. Thanks!