You know, it's funny how my head works. I will drop money on equipment to DO things without a second thought, and that goes double if it's something that I'll use a lot.

A new tool? -no problem.
A weight to throw? -all the time
a gizmo for the boat? -you bet
fabric to MAKE a kilt? -of course
super cheap athletic shoes to wear "around" every day? -naturally

However, dropping money on clothes that I don't wear all that often is like torture to me. It took me three YEARS to finally decide to get a jacket and waistcoat that fit me properly. Instead, I tried adapting sport coats, etc. etc. and looking for super-duper deals on ebay until I realized that it just wasn't going to work. The same goes for shoes. I don't live in dress shoes. I wear athletic shoes and old hiking boots to work, and around town. I might wear these shoes 7-8 times a year, so in my mind it's hard to justify spending a mint on them. What makes it worse is that I think it's nuts to buy shoes over the internet. I mean, I have to put them on my feet to see if they fit, right? I'm not one of those guys who'll buy a pair of shoes, have them shipped to me at great expense, then try them on and if they don't fit then I have to send them back again, ....again at great expense. No. Lots of things are buy-able over the internet, like say....books for example. Shoes? Not so much.