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It’s a different form of movement - pitch, balance, stride length and will vary further with height. And real world walking conditions are vastly different than walking in a wooden floor at home which is where one practices. And not just guys - look on the how-to-walk-in-heels articles in fashion mags and they all advise learning at home. I’ve not had sufficient real world practice to feel comfortable in stilettos although 3.5 inch Chucky heel boots are fine for me. Towpaths these days are mainly for dog-walkers, joggers and cyclists although there are a few historic boats - for show - that are pulled by horses. Narrowboats these days are run in diesel engines although there are a few hybrid and electric ones out there (expensive!)

Hunter boots are great, when I used to travel to Antarctica regularly I wore them a lot - great for Zodiac landings but sturdy enough for moderate hiking as well. I did the last five miles of Shackleton’s hike across South Georgia Island in a pair of Hunter boots

Maybe your experience is different, but what I'm saying is that there is nothing to get proficient at. I mean, assuming the machine is operating properly, there is nothing difficult about walking in stilettos because they are stilettos (on hard pavement at least). In fact, some things are easier than when wearing thick block heels. My issue is the absolute steepness. I hit a wall at about 4 1/2 inches. If I'm really being honest with myself, it's more like 4 1/4 inches. I had to do a quick run to the grocery store yesterday afternoon, and I broke out some round-toed, 4 1/4 inch stilettos that I hadn't worn in a while to run the errand. Once warmed up, I was brilliant. I even got a sincere compliment from a man (how often does that happen?)! But, at that height, I can feel my achilles tendon straining, especially the right leg, with each step. To be fair, I weigh a mere 60 kg. Perhaps thin heels react differently to more torsional force than what I subject them to, but I don't really notice the difference except when I step in a crack and ruin my heel! BTW, are towpaths actually used for towing these days? If so, by what means?

That’s my same circular argument. I don’t wear stilettos much as I am not proficient enough, but I can’t get proficient enough without wearing them. In my case it is complicated by the fact that I am usually moored along a muddy towpath and not only would wearing stilettos be silly, it would just wreck them.