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
“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