In general - I'm a "math guy." If a problem can be solved in my head in math terms - I'm much more comfortable than if it's justified without them.
In my personal life - I've been brought up to appreciate money earned. I've been very lucky to have married someone who has the same appreciation. Spending without justification just never sits right with us. This isn't to say we are "cheap" by any stretch of the imagination -- We merely require some form of thoughtful or researched justification before we spend our money.
My wife, in particular, happens to be a very thorough and "dedicated" shopper. She researches purchases, utilizes discounts whenever available and is someone who unquestionably puts the "market research" time in. As a member of the male gender - there are obviously things I will never be able to understand about the opposite sex and vice versa. I believe, however, that I've used my "math mind" to try and bridge the gap in one case.
I think I've come up with a solution for the question: "Should I buy this ______ (insert woman clothing item here)?"
The Answer is: The "Cost per Wear" metric.
Amy and I have come up with a generic "Cost per wear" goal for her clothing.
How much would you pay to rent a specific piece of clothing for a given night? For nice "going out dresses" for Amy - it may be $30 - for example. If she buys a $300 dress and can realistically wear it at least 10 times - than she could justify buying it. If not - then don't. The more she wears the dress - the better the "cost per wear" efficiency becomes. You can have a different "Cost per wear" metric for Sweaters, Boots, or anything really. (I haven't really figured out if Jewelry passes this test - but my guess is that it's more complicated).
This sounds really dorky - but I think it's a solid exercise. Amy is paying more attention to how many times she wears things (in relation to how much they cost). If things from a specific brand last longer - (and hence have a better "cost per wear"), Amy is more likely to buy that brand again in the future.
I, on the other hand, have been able to help Amy out with her shopping questions, without sounding like a "clueless and standard guy."