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Absolutely! In places where I’ve moored the towpath is doable in heels and there I’ve certainly noticed the difference between that and walking on the hardwood floor in my boat! im not embarrassed by the fact that I like wearing heels - but I would be embarrassed to be seen fumbling around in them.

The problem with the park, and I have this problem also, is that it still doesn't solve the problem of having to learn a difficult skill right out there in front of the public. I suppose there is a case to be made that at our age we just shouldn't care at all, but in this case I certainly do. I'm already presenting myself in a way that is unusual and perhaps a bit shocking, I do not wish to look comical or foolish as well. Isn't that kind of the opposite of what we're going for? I am not sure what the answer is. There are only so many times I can walk back and forth in my garage, and that certainly does not prepare me for the real, uneven, hilly, broken-pavement world.

Whoa! Matching your shoes to the color of your top? That's close to blasphemy. It oughta be the other way round, innit? 😆😆😆

I am not usually a big fan of designer stuff in general, but Miu Miu brand seems to fit me very well. I have three pairs, all of which I managed to snag at a deep discount (used) on either Poshmark or ebay. I wish I could remember what I paid for them, but I'm sure it was well under 100 USD. Those sandals are actually pretty comfortable for what they are. I don't know that they'd be my first choice for wearing to Disney World, but they'd probably be ok to wear to the mall. A parting thought: The other problem with Miu Miu, besides the retail asking price, is that the vast majority of the designs are pretty ugly. Evidently, Miu Miu is Prada's sort of fun, wacky styled line. Also, as I'm sure people are resignedly used to by now, they don't make them above size 42 (which I'd consider a USW 11).

It's an amalgamation of the words "shoe" and "bootie." I don't think they necessarily have to have laces, but they are essentially a very short ankle boot. There may be some debate as to exactly what the definition is, but heck, we can get into an argument here about what the definition of a sandal is. I commandeered a pair of Swedish clogs from my ex-wife, which was my first sort of inkling that maybe I could wear something with a little more elevated heel in public and get away with it. This would have been around 2000 or so.

"Shooties" : lace up booties.

I also went to one of coffee shops in Scotland and posted a photo from it in that tread.

"Shooties"?? I have a few pairs that I have "commandeered" from friends/relatives as well, but most have been worn out by now as well.

OK, sorry, must be confusing you with the fellow you mentioned. Look forward to hearing of your progress, and perhaps seeing some photos.... Don

Because I have to walk a ways down the towpath to do my shopping I have a good sized rucksack for carrying groceries. No problem to put my stiletto boots in and change at the park once I’m off the towpath. The walking surface is good in the park. As for photos you are mistaking me for someone else. I’ve never posted a photo of myself in heels. There was another member who lived in the north of England who used to post pics of himself at cafes. Not me. That said I am thinking of setting up some shots in the park if I can work out some good compositions. Professional pride won’t allow me to post snapshots. So I’ll work out some good angles and backgrounds, practice a bit and see how I go

In the late 70's early 80's, I commandeered a pair of 2 inch shooties from my ex-wife. wore them thru to the mid 90's until they wore out.

A frustrating situation indeed, one I struggle with as well. I also understand your concern about rough terrain/sidewalks damaging your stiletto heels. I have lost many pairs to rugged city sidewalks/grates as well. What kind of walking surfaces does your park have? Decent paved walkways? If so, the heels should be OK. I guess the issue I'm wondering about is having to wear another pair to the park due to poor walkways near your boat. Where will you store/stash you other boots while walking in your stiletto boots? Perhaps you will stash them in a back pack. I'm hoping you will give it a try, you will realize your capabilities/comfort level quickly, so I wouldn't worry too much about looking silly. Make a few short walking trips near the bench, increasing the distance as you feel more comfortable and competent. I'm betting you will do just fine. The only other method that helps me out is having a bootbud or gal pal along for the walk, is this a possibility? I'm thinking that your neighbors are used to seeing you walking in tall boots with heels, so they probably won't even notice the stiletto heels. I always enjoyed your pictures sitting at a coffee shop in your boots as well. D

The "curse of youth" I guess. When we were younger, we tended to be overly concerned with how others viewed us, and thier opinions. Now, that I have racked up some years/miles, I really don't care (with few exceptions) how others view me or my boots. The important thing is that I enjoy wearing them, feel great in them, and feel I look pretty good in them also. Absolutely correct, I have overlooked that issue for sure. Times have changed making it less difficult/dangerous for guys to wear heels.

To everything a season

Yeah, it would have been nice to start earlier, but everything has a time and place. Had I actually started wearing heels when I wanted to, I believe my life would have been harder, not easier. I'm just trying to imagine me wearing heels in high school in the 80s. I probably would have been literally beaten at some point. I may have gone my own way about a lot of things, but I certainly was not ready for those challenges at that time.

Like you I wish I had been able to summon the nerve to wear boots and heels much earlier. It is silly and foolish to allow yourself to be so hobbled by the opinions of others, especially in something that in the bigger scale of things is so trivial. It’s not like wearing heels is a sin, or a crime, or damaging to anyone - it’s simply expressing yourself in fashion. Allowing yourself to have fun. And once you realise and accept that it is such a relief to unload all that useless angst

Yes, living on a boat does make things tricky in terms of wearing heels. Obviously I can wear them in the boat, and while I’m working at my home office. I’ve a nice hardwood floor and can get up from my table and putter around the galley, make coffee, cook meals, and do chores, and in that regard I suppose I am no different than anyone who wears heels to an office in the city- they spend most of their days sitting down at a desk or conference table. I just don’t have the commute! I also don’t have a ready means of practicing and acquiring the effortlessness in wearing heels that is so important. Especially with regards to mastering the 12cm stilettos to which I aspire. Even in the 10cm ones, which I'm fairly comfortable with, I could do with some longer walks etc. I really need to figure out some way of managing this. I can go to the local park, change into my heels and practice there, although I am reluctant to do my practicing in public as I feel silly looking like such a beginner in my 12cm heels - yet if I don’t put in the practice I’ll never gain the skill. And I really want to gain that skill. I also worry about the fragility of my stiletto heels. I know the song These Boots Were Made for Walkin’ - but how far and in what conditions? I’m not at all worried about going out in my chunky heeled ankle and OTK boots - and as long as the towpath isn’t a sea of mud (and it sure hasn’t been lately in our drought) I’m happy to walk to town in them. And on the bright side with my stilettos, I do derive some benefit in wearing them in my “office” simply for the liberated, creative feel wearing them inspires. I’m just not gaining that effortlessness that completes the look.

you look great

Well, I wish I could jump on that time machine as well, not just for the great boots and styles.... More importantly, to accept my true self much earlier in life, would have had so many more years of enjoyment in boots. Oh well, at least I findally came around. I would do anything to help even one younger guy avoid the horrible emotional trauma I put myself through, wasted so many years of my life.

Just found this thread... I don't understand, why would anyone actually want shortened tendons? What possible benefit could they provide? A double edge sword for sure. True, you work from home so can wear nice heels whenever, but your boat and those paths make it near impossible! A bid downside to my recent retirement is not being away on layovers and enjoying my heels publicly. The best I can do right now is slip into my block heeled ankle boots while out do errands by myself. I have gotten to the point of leaving my boots in the car clearly visible to my better half, who is not happy about it. Oh well. I need to get to the point of just putting them on with him present, it will go badly, but needs to happen. It is like you say, wearing tall heels requires competence and confidence. Fumbling around, or trying to stay "hidden" while out in public will draw negative attention and lead to emtional set backs. So, it is super important that the heels you choose to wear fit well, and are relatively comfortable. I'm convinced that many tall heels were never meant to leave the insidde of your home. I was so happy when I found my nine west booties with 4.5-5" stiletto heels, fit well, comfortable, and fairly easy to walk in!

You look great, and I'm betting those tall heels were fairly comfortable

I definitely have different sets of shoes for walking vs. dressing up. There is some overlap, but not a lot. I rarely wear stilettos to walk in, but sometimes I do it just for the fun of it. Here are some recent examples of dress up shoes and walking shoes. I'm sure it will be obvious which is which. Neither of these are 12 cm height difference. Still workin' on that one.

Church outfit of the week, 10 August, 2025. Miu Miu strappy sandals in nude patent. 5 1/2" heel, 1" platform. I should wear these more often. As I was saving the photos to the folder entitled "HHPlace," I realized that I wore this exact same outfit to church about 2 years ago. Shame on me! 😆

@Shyheels Exactly, making it look effortless is what it comes to. @Cali Wearing heels to heal your pain is something different, glad to hear it works for you!

I got into higher heels to shorten my calf so that it could heal. A level 3 tear, they should have operated on it, but with a 65 cm circumference it was just too enflamed. I continue in heels for my hip. I will put my heels on at home and go to work, 8 to 16 hours continuously spent in 10 to 12 cm heels everyday I work. More hours in heels equates to less hip pain.