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 2: Enter all possible output values from picklist in a separate column (in this case, column C)
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:
In your Word template, setup a table with all possible output values Static in one column, and IF statements for each possible picklist output in another (which will create either a checked box or unchecked box)