It's really hard to keep up with changing times in a comic, unless you're Lynn Johnson of For Better or for Worse - she aged her characters in real time, including famously killing off the family dog. One of my favourite mainstream (ie, newspaper) comics is Zits. When I first started reading it in 1997 the parents were of the age they'd have been late teens in the late 1960s - they were portrayed as aging hippies, and all of their musical references were sixties and seventies bands. The strip has continued since then, nearly 30 years, and yet only two years has passed in comic time (the main character, Jeremy, is seventeen, he was fifteen when it started). Now the parents would have been teens in the nineties and Jeremy would have been born in 2007. Unfortunately the creators, who were themselves sixties kids, do not know nineties references well.
Similarly, when I first started reading FoxTrot, I was Peter's age (16) and thus related mostly with him. Now he's still sixteen, and I've even passed his parents in age (I'm 52, they're 43/45).
Most glaring, though, would have to be The Simpsons. Bart was ten in 1989. He's still ten in 2024. Earlier episodes had Homer and Marge in high school in the seventies. Later, they were in HS in the 80's... then the 90's... then the 2000's...