Cost Per Wear: A Useful Calculation?

I've read lots of articles about using cost-per-wear to determine if a clothing purchase is a good value. The basic idea: even if an item is expensive at purchase time, repeated wearings bring the actual per-wear price down to something quite reasonable. The Budget Fashionista has a nice simple explanation here.  And Serene from the Elegant Bohemian wrote about cost-per-wear today (though she looked gorgeous, she wasn't thrilled with her investment yet).

{For us math-challenged shoppers, here's a fun calculator to speed up the decision making -- the Skinny Cow Cowculator.}

Yippee, I love to analyze! (The opposite of my personal philosphy is probably, "Well, that's the way it is.") So here's my take on cost-per-wear (CPW): The concept is a reasonable one for certain categories of clothing.

A good leather handbag is worth a few dollars IMHO. Handbags are such a personal choice, though, and you can rotate through lots of fun, inexpensive bags in a year for the price of one "good" one.  It's amusing to apply CPW to a super-high-end handbag. Here's a fetching one for a cool $5,450. If I wear it 7 days a week for 5 years, that's only Three Bucks a Day for my handbag! But . . . I know I'll never want to wear the same bag every day for five years, will you?

So Question #1 for you, Do you prefer variety, or one/two higher-end handbags? 

Shoes are a no-brainer for me -- my middle aged feet can't tolerate cheap shoes anymore. And a great-fitting pair results in a very attractive cost-per-wear for me, because I will wear them to the nub, and keep them for years. I'm not talking about Louboutins for my modest life, but a great pair of Kenneth Coles, Calvin Kleins or Indigo by Clarks and my feet/wallet are happy. The math works.

Clark's Sandals - Pretty and Practical

Question #2 - What's the oldest pair of shoes you own and still wear regularly? Mine are probably a pair of Naturalizer peep-toe wedges, about $80, purchased four years ago. They are burgundy, and gosh darn it, they really do go-with-everything.

A couple of cashmere sweaters and a high quality wool coat are the only other items I'd permit myself to spend a bundle on. Cashmere lasts for a long time and keeps its good looks, if washed carefully. A nice coat or jacket will do me for a decade in Florida, and makes any winter outfit look more special.

Calvin Klein wool coat - I don't own it, but I wouldn't mind.

After handbags, shoes/boots and coats, the CPW starts to lose its power for me. For example, I used to think suits should be purchased with the "investment" philosophy. But I never really did get my money's worth out of the wicked expensive ones. The styles changed just enough that I looked dated, or I got tired of the cut/color long before the CPW was reasonably low.

Everyday pieces -- cardigans, shirts, knit tops, skirts, jeans, et al -- I just can't spend too much on these and justify it with a CPW. Consignment and thrift shopping have spoiled me for full, high-retail on these pieces. For example, I'd have to wear this beautiful skirt about 75 times to get it down to a comfortable CPW of $2.50. My lovely floral thrifted skirt gets the job done in one and a half wears.

What's your take on cost-per-wear and Investment Dressing?