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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!

They look good but I think the faux suede would get ruined pretty quickly. For sections of the canal they’d be great though

These would do the job, and fit you too! https://hhplace.org/topic/25705-brand-new-asos-recite-boots-uk1112/

Dr Suess was a wise man indeed

Nice! It just so happens that I have two pairs of this style of ankle boots, both from Schutz, and why I have two pairs is beyond me (can you say "impulse buy" on the second pair?). Both are ~4" in height and I wear them with long boot-cut jeans for an rough but elegant look. Oh and forgot to add, yes, I will be wearing these to work in the next few days!

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.

I bought yet another pair of Steve Madden pumps, model Daisie. I bought them because they were purple. Only once I got them, they were only purple-ish. I don't know what color you would call this, but I wore them for the first time today, with pink and salmon attire. I don't really have anything purple to wear with these shoes. As you can see from the picture, they are tall, but not super tall, coming in at 4 3/8". The heels are super skinny, though.

These ASOS 'Recite' ankle boots in black faux suede (not brown as pic suggests) have a sturdy 3 7/8" heel, a round toe and a side zip. Although stated to be UK13, they run slightly small and are a perfect fit for UK11/12, with thick socks if desired. Absolutely brand new and in original wrappings. Very comfortable and discreet - I have an identical pair which I wear outside frequently. I'm asking £22 inc postage; UK only.

That's actually fairly impressive, considering how steep these are! I'm not a big snakeskin guy, and I'm not necessarily a big platform guy, but I kind of like these shoes anyway. "Walking in them is absolutely no issue. . ." I think maybe your definition of "walk" and mine are a bit different, but as long as you're having fun!