I think we have similar upbringings. When I graduated college and my college car was dying, I bought a brand new car-a small car. My mother said, "We never bought a brand new car in our lives!". Strangely within months my parents bought a brand new Oldsmobile.I used to feel guilty over purchases because even though I was raised in a nice but unpretentious suburb, my folks taught my brothers and me to save money and to not splurge. Get things on sale whenever possible. They could certainly afford to pay full price on most anything I'm sure, but they both love the thrill of a bargain (and have wonderful taste to boot!).
A lot of that has rubbed off on me, but a part of me loves to spoil myself with luxuries. My Mom thinks spending $200 on a bag is a lot. There are a lot of great bags out there at that price. We went bag shopping for her awhile back and I found a wonderful cream colored classic Gucci which would suit her to a tee. But she didn't like the idea of spending $1000+ on a bag. She'd probably flip if she knew how much I've been spending!
My mother would constantly take back jewelry my dad would give her at Christmas, saying he spent too much money. She would flip over my purse collection.
I was raised like this and I think it has had somewhat of an opposite effect on me!