(Sorry, this is so long!)
Most of my splurge items are done with a penny pinching attitude. For example, I like nice, well made clothes, but can't afford them. So, I buy them used.
Shoes are a different matter. I will spend a pretty penny on a well made, durable, attractive, pair of boots. I live in an area that is rainy nine months out of the year. I wear my boots on an almost daily basis. I am on my feet, a lot of the day and I like being comfortable. I also feel darn attractive in my boots. My current pair cost an arm and a leg, but have lasted years. To me, it was worth the money. We buy my SO expensive boots as well. His have also lasted years, and have been drug through sound water on many, many occasions. It's important that while working nights on the water, his feet are warm, dry and comfortable.
The kids do (mostly) hand me down, sale or gifted clothes and I have been able to find them expensive, gently used boots. Their grandmas/nana love buying them shoes and clothes. God bless the grandparent impulse to spoil.
Our cars were used, but are also well made, hunted for months and are safe.
Our house was a short sale and had a collapsing roof, two bathrooms in disrepair and was being eaten, from the outside by blackberries. It's twenty minutes from town. It was...a deal but meant work. Doing things DIY, with family help, and trades w/ more competent friends we've been able to do A LOT, so hopefully, when we sell we will get a return for our work. I'm learning a lot working on it.
Bottled water grinds my gears. I'll be honest. Watch the movie "Blue Gold" and you'll prob. never go back. Likewise, I don't do paper towels or paper plates/napkins. I do buy tampons and pads. Note to self: look into a diva cup. I don't have makeup (had some cheap stuff and the kids got into it...), but am going to splurge because I'm getting married in a few days.
We eat what we have and wait till town before adding more to the fridge. I do feel strongly about the ingredients I buy and make an effort to provide a well balanced diet from fresh foods.
I buy a lot of our tools and gadgets (camera for ex.) from individuals or pawn shops. I love haggling, and it's O. of the few places where that is culturally acceptable. The internet has also been kind to us in that regard. I don't pay for cable, but do get netflix and the internet. We don't go out to dinner more than once every few months...and then we do lunch. It's cheaper.
Well, thats enough out of me! Love this question, BTW