What's the most you have spent on a pair of shoes? What was special about them?

I didn't spend it, but I have a pair of bespoke slip-ons that my late father had made by John Lobb of England for about $3000. Nothing special about them other than that they fit my feet perfectly and are very comfortable for dress shoes. But I have few occasions that call for dress shoes, so I think I have worn them once in six years since he died.

$300!  The only thing "special" about them was that they were black (required color for work) AND they fit my feet (miracles).  At the time, the brand (which I can't remember) were a top of the line shoe and made of leather (figures that the only shoe in the entire shoe store that fit me would have to cost a months wages).

I got my money's worth though.  I wore them to work, 40+ hrs/day, 5 days a week ... and it took 5 years before they finally wore out.  I didn't simply stand on my feet all day, I walked 5 miles around the store each day (pedometer), throwing load and helping customers.  Since I'd memorized the entire store (it wasn't a small store either), everyone either asked or sent customers to me to find things.

About $170 about 5 years ago. Hiking boots - not something to go cheapo on. They are incredibly comfortable, and I'll continue to use them for years.  

$150. Steel capped safety boots.
I don't buy expensive shoes as a rule, the cheap ones are just as comfortable and finding anything my size is tricky, I have very small feet for a man.

$380 ---daughter's hiking boots

Not sure if that's most expensive but I thought it was too much at the time. 

Probably about £40 for a pair of safety-shoes, for work; though about £70 for a pair of walking-boots.

I have these 

I can't recall the last time I bought dress shoes.  I have so little occasion to wear them that whatever I already have will do.  I buy New Balance sneakers though and the price has gone up so I try to get them when they're on sale and have paid probably $80.  I do recall when I was on my first job I bought a pair of black and white high heels.  They were made out of some reptile skin (can't recall which) and while I can't recall how much I paid for them, it was an outrageous amount at the time, but I loved those heels and got a lot of wear out of them.