A History of Short Words

From the New York Times Crossword Puzzle

UNHIP

Thu, 21 Dec '23
Not cool
Wed, 4 Oct '23
Squarish?
Mon, 25 Sep '23
Not cool
Sun, 27 Mar '22
Square
Thu, 24 Mar '22
Not cool
Mon, 18 Oct '21
Not with the times
Wed, 27 Jan '21
Square