I think we are in a very similar place to what both of our parents were when they started out. We might be a little worse off - we went straight from grad school to having kids, and I can't afford to stay at home like my mom/mil did.
They both will occasionally make comments like...well, yesterday, I was trying of find a sleeper for LO. I had been looking for weeks for something at all, let alone something under $7. Their mall sold Carter's, so I got one even though it was $9. She started talking about how she loved the Little Me brand, but could never afford it when they were first having kids and her aunt would send her one and she thought it was so nice. But I'm "lucky because I work and can afford stuff like that."
I don't know, maybe Little Me was nicer then? I mean, I could never afford stuff like Boden or Gap, but if LO desperately needs a sleeper I can get him one...
Then we were shopping for a comforter. I was stressing over the price ($80) and she said, "well, it's not expensive, just buy it until you find something you like and replace it!"
My mom does the exact same thing. I think they want to one up how "poor" they were and we have it so much easier (not saying we aren't lucky, but we are typical just starting out and not rolling in it parents with student loans and a mortgage and diapers to pay for!) But on the other hand, they've both done well and completely forgotten how much stuff costs. I asked my mom if $20 was a good price for a shower head shopping with her once and she said, "um, is $20 a lot to pay for anything?" Lol YES!