Topic
Here's some guidance for outputting Multiselect Picklist values with checkbox's. This will involve a combination of Excel Connected Data and Word Conditional statements.
Instructions
Setting Up Excel Template (note that column E is just for visual reference and not necessary)
Step 1: Tag the Excel template with tag from the picklist field

Step 3: Setup Formulas and create tags for Connected Data in separate column (in this case, column D). Note that the formula needs to be adjusted for each row (Apparel would be ‘=ISNUMBER(SEARCH(C3,A2))’

Step 4: Setting up Word template:

https://help.nintex.com/en-US/docgensf/Templates/ConnectDataToTemplates.htm