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When I was in school (back in the covered-wagon days), if you didn't have Levis or Wranglers, you weren't cool. Or if you had K-Mart specials for sneakers instead of Pro-Kids or Converse. So styles (and the expense of "cool" clothing) may have changed but the sentiments and peer pressure has not. (Though it may have become more intense, I can't judge, having no kids.)
However, what seems to have changed is that some parents today really are invested (and investing) in what will make their kids cool. Back then, my folks said, "Just wear them. They're just sneakers." But my peers and those of the next-younger generation of parents who heard such comments in their youth are now saying to themselves, "I won't do that to my kids!" And so they are spending through the nose to ensure their kids have every cool item they want. It's the parent-as-best-friend syndrome. And it's creepy not just because of the JonBenet factor but because it suggests a fracturization of parenting.