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About 5 years ago I had a (much) younger woman thank me for wearing heels. She loved heels but had succumb to peer pressure and stop wearing them. Seeing me in heels everyday gave her confidence to again wear her heels. And she was happier. Yes, she liked sitletto pumps.

I guess I never really read the original post carefully, which is rather unlike me. Now that I have read it, I have some real advice. I feel I can give real advice because I've been there. Stop with the 200 pairs of shoes for your wife. They're not for her anyway, and you know it. Get your own shoes, and then you will never feel the need to pressure your wife to wear heels when she doesn't want to. This is not a perfect solution. It may create other problems where none existed before, but it will solve some very fundamental problems that you are obviously having. I'm not being mean, I have just been there myself.

The font option appears to be back. It was gone a few days for some reason. I have been a follower of this site since the Jenny days (circa 2000), but I was up until recently programmed to believe that heels were only for women. Had I stayed married to my ex-wife, I wonder how my fashion proclivities would have turned out. As a result, I actually joined fairly late, and it took me quite a while to get used to the sight of men in heels, including my own reflection in the mirror. I was a little taken aback when I got here finally, and was not necessarily welcomed with open arms. This place has evolved quite a bit within the last decade. True, it's almost dead, but it's friendly. @Laurieheels was a favorite of mine back in the day. Punching in the name, I see that she is still technically a member here. She was inspiring to me because she wanted to get to the point where she could wear very high heels every day as her normal footwear. And I really don't remember the denouement of her journal, but I do remember progress documented. And I thought to myself, "I wish my wife would do something like that." What I did not realize at the time is that what I really meant was, "I wish I could do something like that." Here I am, some 20 years later, living the dream. Of course, my job does not allow me to wear heels as much as I would like, but it's enough. I think I can reasonably say that I probably pound the pavement more than anybody, maybe not timewise, but certainly distance wise, and although I've never learned to properly walk in 5 inch heels, I have pretty much mastered 4 inch heels (more about how that is so untrue in a future installment), and I guess I'll have to be satisfied with that.

Happy anniversary! You prompted me to discover my own length of servitude - 20 years and counting. Makes me feel really ancient. You can easily alter the font; the 'Font' button is on the top row at the right. I too am not keen on sans serif for text, but am usually too lazy to alter it - but this time have done so to my preferred Times New Roman, 16pt.

I went to a high school jazz band concert this week. I saw what I expected to see, a lot of low-to-mid block heels, and largely on strappy sandals. Despite the temperature being around the freezing mark, there were an awful lot of sandals in the band. Perhaps it comes of these younger girls having but one pair of dressy shoes, and they happen to be sandals. Heels do not appear to be dead, they're just a lot lower and clunkier than they used to be. Which brings me to the reason for this post. On my way out of the building, I saw a girl/young woman wearing actual high heels. She was obviously not in the show, because otherwise she would have been wearing black, and I couldn't tell you exactly how old she was, but she looked quite young, had braces on her teeth, and was wearing this rather outlandish flannel blanket/dress thingy. I don't really even know how to describe it. It didn't look horrible, but it did look rather odd with her black strappy sandals. They looked pretty similar to all the other girls' sandals, except they were easily at least twice the height. Chunky block heels, but I would estimate about 4 1/2 inches tall with maybe 1/2 inch platform. In other words, actual high heels. So they are still out there, even in Gen Z.

I have evidently missed my HHP anniversary, but not by much. Evidently, I've been on this site for 12 years! I wonder how this would have all gone without this site. I had already made up my mind that I was going to wear the shoes I liked about six months before I joined here. I'm sure that my fashion life would have been different, but I'm not really sure how. I guess it's been good to know that I'm not the only one, but I've been used to that my entire life, so I don't know that it would have been a deal breaker. One thing I have noticed is that for my anniversary, I no longer have the option to choose a different font than this default sans serif font that I'm not particularly fond of.

Do we get "retro month" entries? That is, if I missed submitting an entry in, say, July for example, can I submit an entry now for that month? I ask because I wore this super cute outfit to the office and after the day was done, I went to the Ulta (cosmetics) store for a few products. While there, just about every woman in the store complimented me on my outfit and needless to say, it was quite flattering.

I had occasion to go the bank yesterday. We got off work a little bit early, and I decided I needed to move some money around. This time, I made sure I was cleaned up, looking halfway presentable, and wearing heels. I chose burgundy colored pants to go with burgundy Carressa mary janes. I considered wearing some super stiletto-y Steve Madden pumps, but thought the mary janes were a better choice for what I was trying to accomplish, which was to talk to the bank lady about heels. I entered the bank with my paperwork in hand, looked around for an open teller (and the high heeled bank lady), and soon a teller called me across the lobby to her counter. No sign of the bank lady. Figures. I went on about my business with the teller, and the next thing I knew, there was this person standing right next to me, which just goes to show that you can't always be situationally aware unless you make a constant effort to be. The person who sneaked up on me was the bank lady, and she said, "I don't mean to bother you, but your shoes are incredibly cute. I heard someone walking across the lobby who sounded just like me, and I had to see who it was. I'm glad it wasn't just somebody wearing cowboy boots, and WHERE DID YOU GET THOSE SHOES?" Whoa! That was not at all how I figured this was going to go down. You would think that after what, 12 or 13 years of this that I'd be perfectly comfortable with this sort of encounter. I did manage to get out my line that it was indeed heartwarming to see someone out there who still wears heels besides me. Mind you, this is all right up there at the counter in front of the teller who was helping me. So as it turns out, bank lady wears heels every single day and loves wearing them, and the rest of the people at the bank think she's crazy. I think she was glad to have someone else tell her coworkers that heels don't necessarily have to hurt at all. I don't think we gained much traction on that assertion. After the transaction was over, I went over to the bank lady's desk (I still don't know her name), and we talked about shoes for another five minutes or so. Her boots on this day were nothing very special, they were plain black with slim (not stiletto) 4 inch heels. She said she had most of her extensive shoe collection already packed away for the move. Move? Now for the bad news. This interaction will never happen again. Evidently, today (Wednesday) is her last day at the bank. I asked her where she was going to, and she said that her husband had gotten a new job in a town about 75 miles away, and that they would be moving there. I know the town reasonably well, and we talked about her impending move. I wished her well and departed. It's not really a big deal, but that's exactly my luck. I'm going to be the only one again. Sigh. At least you won't have to read any more stories about the bank lady, and I know for sure she doesn't think I'm a creep for liking her shoes.

I think some of the blame for the demise could be put on husbands and boyfriends too. My wife LOVES high heels, but sometimes on a date we ended up walking much further than we thought, or we ended up standing longer than anticipated. Other times her new shoes just hurt her feet quicker than anticipated. It was no big deal... my wife kept a pair of soft flats in her purse. They took up some room, but were no heavy, but more importantly were always there as a way out. While I preferred her to be wearing high heels, and thought it made a much more poignant fashion statement, the truth was her heels hurt her feet, so she switched to black flats. I think to some degree if husbands and boyfriends adopted that concept, it would not only be supportive, their loves might wear high heels more often since they have a way out of painful shoes. But it need not be just black flats. Having Keds at the ready, or even going to places where she can go barefoot are all painless alternatives. And alternative shoes can be kept in the car, the inside pockets of a mans suit jacket, etc. Its just the concept of them having a less painful alternative that might help make wearing high heels a little more attritive then the person thinking, 'It's going to be a night of painful feet".

Thank you to all for the wonderful responses - I truly appreciate the support and kind words! As I have made known in several previous responses to other threads, had I not found this forum and read the stories of other men venturing out in heels for the first time, I do not know that I would have ever found the courage to do so myself. Given how far I have come in just about a year, it seems somewhat foolish that I did not do so earlier in my life. As I was driving home from the office in a ridiculously cute outfit I wore today, I was thinking that it is almost a year to the day when I first wore heels (boots, actually) to the office. Although ~95% of the shaft and heel were covered by long pants, I was still so nervous about doing so, and that someone would "see" my footwear and take note of what I was wearing. Then, after my work day was done, I headed out for a quick haircut and as I was waiting in the salon/barbershop, store, I was so nervous my hands were sweating. When my name was called, it was a "here goes nothing...!" moment. I was not ready to have anyone see me wearing heels at that time but, admittedly, it was a thrill knowing that I was "secretly" doing so. Now, a year later, I could not possibly care less what anyone may think as so many people, at the office and in public settings have seen me in heels, that it has become routine. I do not consider myself to be "Superman" or the like when comes to wearing heels out in public but I realize that if someone has an issue with it, oh well...not my problem. I truly do not know why I have so quickly overcome my fears of wearing heels in public. I think that once the first few times were "under my belt," so to speak, it just became easier and easier to do. Not to sound like a broken record but the words of Dr. Seuss have truly taken on a new meaning for me..."Those that mind don't matter and those that matter don't mind." Well, enough of my rambling...Thanks again to everyone! Richard Photo - the aforementioned "ridiculously cute" outfit for work today!

November's entries - I think I wore the orange turtleneck outfit to work...definitely wore the red/maroon dress to the office!

Here is an example of what I mean by "near stiletto" heels. These Michael Kors sandals, which I wore to church yesterday, feature heels which are 7/16", or 11 mm, thick. That is not really a stiletto, but the heels are so tall that they perhaps give the illusion of being stiletto. Were they only three inch heels, there would be no question that they are merely "slim" heels. Of course, your mileage may vary. Some people would put this in the stiletto category even at 11 mm. I'm still going with 10 as the maximum. The other interesting thing is that despite their thickness, I would put any of my Steve Madden stilettos ahead of this pair as far as sturdiness, even with much thinner heels. As far as I'm concerned, thicker does not automatically mean sturdier, it really has more to do with the rigidity of the shank.

Got a couple of pictures this week. One is the church OOTW, featuring a gray color palette, which may be an oxymoron. The second is Casual Saturday, when I decided to wear my new boots, which are rather on the chunky side.

Stiletto heels are fragile in the sense that they are very easy to damage from stepping down in some sort of gap in the walking surface. I have never found that the heels themselves are the weak link--it's the shank. For those of you who don't know, the shank is a strip of stiffening material, typically metal, that runs below your foot between the inner and outer soles, and connects the heel with the front of the shoe. I have broken exactly one heel in my life, but I've broken several shanks. Once the shank breaks, it feels like the heel is broken because it just caves in, even though the heel itself is still securely attached. I also have a couple of pairs in that 10 to 12 mm "near stiletto" range, but ironically, they are some of the least stable feeling shoes I own, and it has to do with the shank, not the heel. I'm not making a plug, but I have over a dozen pair of Steve Madden stilettos in various styles, and I've never had pair of Maddens feel anything but rock solid when walking. The heels on these shoes range from about 10 mm all the way down to <7 mm. If you didn't see what you were wearing, you'd never know that you were walking on heels that thin. To be fair, I also weigh 60 kg. That may have something to do with it.