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It will no problem. Trust me. I wear knee boots a lot - indeed I am writing this at a pub in Yorkshire where I am having dinner on a busy Saturday night. I am wearing grey suede OTK boots with low heels over skinny jeans and nobody has given me a second glance. Ok, they are low heels but OTK boots all the same. No issues. At all

I think I will start with a low heel knee high boot and hopefully progress from there. Absolutely want to be confident I can walk more than a few steps.

Sounds like you’re really copping the snow! Over here in the UK we’re getting a blast of what we call cold weather - which means about -3°C where I am (that’s about 26°F for you guys). I have to say though the British cold can be more unpleasant than the temperature figure suggests. I think it’s because there is a rawness to it that just seeps into your bones. At any rate it’s perfect weather for knee and OTK boots! I am certainly getting good use out of mine! I like the boots you were wearing. I’m quite a fan of low- to mid-heel knee boots - a nice combination of stylishness and everyday practicality

I think you fundamentally misunderstand what this site is all about. It's not that your photos are technically inappropriate in any sort of legal sense, but the boundaries you are pushing are irrelevant to us. We are trying to change society one person at a time. You are playing dress-up in front of the mirror. There's nothing wrong with that, but it doesn't really fit well with this site. We're simply not pushing "raciness" in any way. We are about practical advice, general fashion advice, and stories about interacting with the public as guys in heels, and hopefully gaining some acceptance as such. I hope I don't come off as a jackass, I'm just trying to put the issue in perspective, calmly. I can't say that I speak for everybody here, but I know I speak for quite a few.

I really don't miss this.

"Stuff" has gotten real here. I have not left the house for about 36 hours. Let me rephrase that. I have not gotten in the car for 36 hours. I certainly have been outside for a substantial amount of time, clearing snow. I will do so again today, not because it has snowed more, but because the winds have kicked up, and the snow has drifted substantially over what I cleared yesterday. Before I get off the subject, @Jkrenzer, I now know what you mean about snowpack, and it makes sense. It also seems like one of those things that I will feel compelled to study in more detail, even though I know it won't really affect my footwear choices in any given situation all that much. I like my block heeled boots mainly because the shafts fit my calves better, and because they are less "cheap" looking, not necessarily because they are block heeled. Speaking of block heels, I spent most of the day in these knee high low heeled boots from Easy Spirit. I did not buy these for myself, but they have turned out to be handy in several situations, one of which was this deep snow. I wore them because I realized that I had left my real snow boots in my car, which was then buried. By the time I got the car unburied, I realized that the Easy Spirit boots are superior to the purpose made snow boots in every way except warmth, so I kept them on. Being as I was only outside for less than an hour at a time, and I was doing physical labor, warmth was not an issue. Anyway, I am glad that my dad bought a bigger snow blower than he thought he needed some 15 years ago, which is now mine. It's not too big. I should be thankful that I have the equipment to dispatch the job easily. I may grumble about it, but this machine makes pretty quick work of what would be an incredibly daunting task if one had to do it by hand. The story is that my dad went down to our local hardware store to buy a snow blower, and they had run out of the model that he really wanted, so he wound up buying the next model up, because they had one right there that he could take home. That was serendipitous, because the model he really wanted would have turned out to be unsatisfactory in the years to come. Despite being equipped with the notoriously troublesome Tecumseh engine, I've kept on top of it over the years, and it hasn't caused me a bit of trouble. Thankfully, I don't put a lot of hours on it in a year. For the third photograph, this is what I had to deal with last night. Snow drifting over my intake pipe for my furnace. This causes it to quit working. I had to go out twice and dig it out last night. I must have accidentally created some kind of fortress, because the furnace is still working fine this morning as I write this. I was mentally prepared to put on my coat and boots to go out there and shovel it out, but I didn't have to. I did put that photo up on social media as a PSA to all my local friends to not panic if the furnace quits working suddenly. I got a message from a dear friend who lives in Buffalo, NY, saying "You guys have more snow than we do right now!" Edit: Pictures are in reverse order somehow. You'll figure it out.