My mother was cheap. She would spend $2.00 extra in gas to drive to the next town to save $0.25 on an item. I love my mom and I'm not trying to talk poo on her, but she didn't understand the difference between a product "being cheap/inexpensive" and "being a good value." It drove my father and me crazy when she would buy something that just didn't last as long or perform as well as the next step up.
I like to think that I have an eye for a "good value." I buy almost all of my clothes on sale. However, I'll spend more on dress clothes than street clothes. My reasoning is that dress clothes will always be in style, and street clothes are generally trendy. A good amount of my music gear was used stuff (the best music deal I ever got, please don't hate me: Bought my Mesa 400+ for $500

). With the exception of a few makes and models, I've never seen a brand new vehicle as a good value, especially considering that you can find a used with with a couple miles at a significantly lower price.
With that said, there are things to me that are worth paying top dollar for and things that just aren't. As a musician, having a lot of money tied up in a rig or bass isn't no thang. It's part of my livelihood, so having top-level gear is important. On the other hand, I'm not a big gadget person, so I don't need the latest and greatest cell phone. Also, I've never been a "name brand person," especially when it comes to clothes. I think some of these shoes, like Nike, are obscenely priced, especially when you consider that it's not exactly top level tailors putting them together.

I do like certain clothing brands, though, because I may like their fit or find that they last long.