In all versions of Windows starting with Vista, Microsoft removed the ability to add custom columns to Explorer unless the file itself can store it and has a property handler installed for that file type. There is a project on CodePlex:
https://filemeta.codeplex.com/ which lets you register a property handler for any file type and maps those properties to NTFS alternate data streams (like Windows XP and Windows 2000 stored tags). Then it can be indexed by Windows Search and show up in Explorer and be searchable via the Start Menu.
Here is how to tag any file and have Windows Search index those properties.
1. Download and install FileMeta from here:
https://filemeta.codeplex.com/releases/view/121762 2. Run the FileMeta File Association Manager.
3. Locate the file extension for which you would like to add tags/keywords.
4. Select it and click "Add File Meta Handler" button, and close this tool.
5. Go to Control Panel -> Indexing Options -> Advanced -> File Types tab. Make sure that this extension's properties (and file contents if you want) are indexed. You may have to rebuild the index.
6. Now just open the Properties of whatever file type/extensions that you wish to add the tags to. Go to the Details tab and add them.
7. Windows Search will index them, then they will show up in Classic Start Menu.
Folders don't need this. Adding any folder to Indexing Options makes it searchable from the Start Menu.
Read the
Start Menu search box usage guide to understand it in detail.