But I can fix the issue by trashing the Office 2011 font cache and then restarting Word. I've had similar issues with Word 2011 for Mac - oftentimes the true Bold and BoldItalic for Adobe Garamond won't work. But in Word 2016, when selecting Adobe Garamond, there's no true bold or true bold italic when I select 'Bold' and/or 'Italic' (nor is Adobe Garamond Bold listed as a separate, standalone font in the menu)- only regular and italic.
For example, I have Adobe Garamond Regular, Bold, Italic, and BoldItalic installed (I had uninstalled Semibold and SemiboldItalic because I wanted the 'Bold' to appear as Bold and not Semibold when selecting 'Bold' in Word). Adobe fonts don't appear correctly in new Word 2016 for Mac (and there are problems with Word 2011, too).