It's so interesting how you cost trackers slice and dice everything. I am also very analytical, but I have never tracked actual CPW of anything. Going back a few years, when I relied mostly on thrifting, consignments, and flea markets for what I wore (when you could still get great things for a song), I would often mentally tally up the purchase prices of everything I had on (minus specs) and proudly note that the entire ensemble, including jewelry, was less than $100 -- or even $50 -- or sometimes as low as under $20.
Since lifestyle/work and location changes, I've switched back to buying mainly new items (in many cases, thrift prices approach new prices now anyway...it's shameful) and have raised my average purchase price a LOT, relatively. It's up to like $25! (OK, well, $60 for shoes and boots, with a preference for leather vs. synthetics.) I am still an insanely bargain-oriented shopper. Most things I have bought this year (so far, 55 clothing items, 7 pairs of shoes) were 50% to 70% off original price. Most expensive item so far? $75, which was half price.
I am OK with raising my bar here and buying this many things because I seriously needed to update and fill in after a few years of buying very, very little. If I'm accurate, I spent less than $300 on wearables in ALL of 2013, which was pre-YLF.
So, I build in a low CPW up front, and that works for me. Just like with TV shows and movies, I don't care if I'm on the bleeding edge of a style the moment it comes out...I figure that I will be wearing a carefully-chosen item for at least a few years because I tend to go for simplicity even in trendy pieces and hope things don't date super quickly (a risk we all face, bah). Plus, lifestyle makes a huge diff. I work at home and don't need dressy things much at all anymore. Major bottom-line savings there.