But true Bold and BoldItalic are nowhere to be found. Interestingly, if I reinstall Adobe Garamond Semibold and Semibold Italic, Word 2016 will give me true Semibold and SemiboldItalic when I select 'Bold' and 'Italic' in Word. (I realize this sounds like an Office or Mac issue, but it only happens with Adobe fonts.) Microsoft will not release any more updates for the application suite after that date. Two upcoming events could make it unsuitable or even unusable in the future: Microsoft is ending support for Office 2011 on 10 October 2017. I can't seem to identify any such workaround for Word 2016. If you still use Microsoft Office for Mac 2011, it’s time to make some decisions.
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).