I know it is hard to part with a single pair of heels but I have learned how to do it. I don't know if it will be helpful, but I try to have at least one outfit for every pair of heels/boots I own. If I can not match the footwear to an outfit, then it gets donated. Likewise, if the shoe does not fit, so to speak, I can easily part with it without feeling "bad" about doing so. I do not want to get into the habit of impulse buying and before I purchase and pair of footwear, I think about where I could realistically wear them. I also think of if I have an existing outfit to match or could easily put one together so that buying that "must have" pair of heels is meaningful. I was recently in a store and noticed a pair of black kitten heeled pumps that would be highly suitable for the office. As I was seriously thinking of buying them, I thought, "Wait a minute, I have at least two pairs of office appropriate black pumps." I asked myself if I really needed them and determined that I did not, so I bought the blue ones instead.
I, like most of us, have heels that are probably most appropriate for attendance at a drag show (not that I am complaining...if you want to see mine, check out the last page or so of the freestyle pictures!) and would never wear to the office. I have heels for three different occasions: for running out to do errands; going to work; and working from home. My running out to do errand heels are kind of a "throw on and go," where my office heels are very conservative (low heel pumps and ankle boots) while my work at home heels are the tallest of the tall. I also try to have heels for each season - winter, spring/autumn, and summer. This way I can have a variety of heels so that each has a chance to be worn with some degree of frequency. I'm not necessarily the one for flash or over the top embellishment, so a pair of comfortable simple black pumps will always work for me. I get it though, as I am always looking to find that "perfect" pair of whatever but given so many factors, most of the time I am just web browsing. I would rather invest money in quality than for fashionable and cheap.
Well, that seemed to be a whole lot of nothing on my part....