Here's the story of my shopping life:
The items I get for mere pennies are the ones I wear most often, while the 'investment pieces' that I justified spending extra bucks on are rarely worn.
There must be some psychological reasoning behind this phenomenon.
Take for example, the outfit I wore yesterday (below). The skirt is one of my very favorite wardrobe pieces. I look forward to wearing it every fall. I got it out of a free bag about 7 years ago. The turtleneck was purchased at Macy's last spring on uber-clearance, and the brown, short-sleeved sweater is fairly new-to-me from Valu Thrift. Excluding my Steve Madden pirate boots, the whole outfit cost me about $10.
If my house was on fire and I was able to rescue just one outfit, this would be it. There is just something about it that reflects my personal style like nothing else I own. Perhaps I have a deep-seated desire to be a librarian. Ok, it's not that deep...admittedly, I would absolutely love to be a librarian. An awesomely dressed one.