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While explaining an answer on hyphenation, (This was the question)

I had a bit of trouble explaining where hyphenation should be used and where it should not.

For example, consider the following two sentences:

  • His entry was less than impressive.

  • His less-than-impressive entry let down the audience.

I know instinctively that the second sentence must use hyphenation, but am unable to explain why this is so. I've heard that the word in the second sentence is attributive, but I'm not sure what that means.

Could somebody give a thorough explanation on when to use hyphenation in adjectives and when not to?

Other such examples are: know-it-all, devil-may-care, holier-than-thou, America-first, cloak-and-dagger, fairy-tale, drug-induced, kill-time, and many, many more(which I don't seem to recall now)!

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    The Chicago Manual of Style (and it is a style question) has nine pages on hyphenation, which is often a matter of clarity and judgment. Chicago follows Webster, and recommends consulting a dictionary as a first source.
    – Xanne
    Commented Jul 28, 2017 at 8:12
  • Harry, huge numbers of people think adjectival hyphenation is so difficult, they'd rather it didn't exist, or had a simpler name. In fact, if you string together a bunch of words and use them to describe whatever follows then the strung-together words need hyphens to do that stringing. Yours are above-posted examples are excellent.
    – Robbie Goodwin
    Commented Jul 30, 2017 at 22:46
  • @RobbieGoodwin Thanks, could you develop on that and give an answer? I've never had to wait so long for an answer on Stack Exchange!
    – Myungjin Hyun
    Commented Jul 31, 2017 at 10:17
  • Yes but what with Google, Xanne's and my comments, what remains, please?
    – Robbie Goodwin
    Commented Jul 31, 2017 at 23:43
  • @RobbieGoodwin I guess nothing much remains! Thanks!!
    – Myungjin Hyun
    Commented Aug 6, 2017 at 12:49

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