You don’t become cooler with age, but you do care progressively less about being cool, which is the only true way of being cool. This is called the Geezer’s Paradox

@juglugs

“The Monks of Cool, whose tiny and exclusive monastery is hidden in a really cool and laid-back valley in the lower Ramtops, have a passing-out test for a novice. He is taken into a room full of all types of clothing and asked: Yo, my son, which of these is the most stylish thing to wear? And the correct answer is: Hey, whatever I select.”

@terrypratchett, Lords and Ladies