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In the very footer of this page: > Historical note: At the end of the 20th century when this was written, "cool" was an epithet of approval particularly among young, indicating trendiness, quality, or appropriateness. In the rush to stake our DNS territory involved the choice of domain name and URI path were sometimes directed more toward apparent "coolness" than toward usefulness or longevity. This note is an attempt to redirect the energy behind the quest for coolness. It's 2020 and "cool" still has that same meaning, as an informal positive epithet. I believe "cool" is the longest surviving informal positive epithet in the English language. "Cool" has been cool since the 1920s, and it's still cool today. "Cool" has outlived "hip," "happening," "groovy," "fresh," "dope," "swell," "funky," "bad," "clutch," "epic," "fat," "primo," "radical," "bodacious," "sweet," "ace," "bitchin'," "smooth," and "fly." My daughter says things are "cool." I predict that her children will say "cool," too. Isn't that cool? |
> Slang meaning "superior, classy, clever" is attested from 1893. Sense of "stylish" is from 1922.
> A 1599 dictionary has smoothboots "a flatterer, a faire spoken man, a cunning tongued fellow."
It may be time to bring that one back. "Did you see Keith chatting up that girl at the bar? Total smoothboots."
https://www.etymonline.com/word/smooth