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Being in North Carolina my biggest issue is the heat. Several pair have lost the bond on the soles from either walking on sun baked pavement or the few times I've left them in the vehicle with the windows up and in sunlight.

I had to laugh when I read this. On Tuesday, I wore a maroon turtle neck (Express women's), grey Flexx straight leg jeans (also Express) a large hoodie (it was cold) and my standard Steve Madden wedges.

I can't really define it, but I know it when I see it. What is elegance? Is it even a goal of mine? I am way more interested in elegance of movement than I am in creating the perfect outfit. And I'm not even very good at that. Having said that, I still refuse to throw on a pair of heels with anything I consider to be workwear (and by work, I mean the kind where you get dirty), as I insist on looking somewhat presentable while wearing heels. However, I'm afraid I will probably continue to throw together my outfits at the last minute on the fly, and hope for the best. Elegant? I think not. Presentable? Attractive? Maybe.

I agree. Fashion and style is not something that can be measured with a tape.

So, I thought an update may be necessary. Probably not though.... I have been giving much thought to this topic and have fielded and read a few words of well spoken advice. Thus, I have arrived at the conclusion that heel height is not always that important. I have come to believe, in fact, that what is important is not so much what is worn but how it is worn. I would argue that one can appear equally as elegant in flats as a pair of 5"/12cm heels. Take today's outfit for example. I was wearing a maroon turtleneck, khaki dress pants, and brown Miz Mooz (brand) 3.5" heeled oxfords. The colors matched perfectly and I accented the outfit with a warm colored short scarf, 15mm rose gold hoop earrings, and a brown belt. Overall, I thought the outfit was gorgeous and reflected a sense of elevated style - simple but well matched pieces. Compare this to the previous day's outfit which consisted of a black/grey/white color block long sleeve shirt, a knee length black skirt (BTW - my first time wearing a skirt to the office!) and a wonderful pair of almond toe, black knee high harness boots with a 1" heel. Again, simple but well coordinated pieces. Although the two outfits were very different in tone and appearance, they both displayed a sophisticated and professional style. I felt equally comfortable in both. Tomorrow evening I am attending a small reception for the opening of an art exhibit for which I will be wearing a black/white sweater, black pants, and black leather loafers, along with a black Spanish Beret (made in Spain but found and purchased in Ghent last April). Once again, simple and elegant. I suppose the point to all of this is that, although heels are wonderful and I will continue to wear them as often as possible, one does not always need to wear the highest heel possible in order to display a sense of style, class, and elegance should that be the desired look. One can have great style in very low heels (e.g. kitten heels) or even flats provided that the outfit with which they are worn is of the same caliber. To me, I believe classic styling of shoe/boot and outfit has always spoke loudly about a person as much as current trends; classic styling will never go out of style as far as I am concerned. Thus, low heels can be just as alluring as a 5"/12cm stiletto; black kitten heel pumps/slingbacks will always be supremely elegant regardless of how tastes and styles change or fade. If I had to provide an example of such, I would say look no further than Kate Middleton (or Jackie Kennedy) as she can make flip-flops or house slippers elegant. So, in essence, the height of the heel is not as important when compared to how it is worn. Flat is not necessarily boring and very high is not necessarily "trashy."

I too have several pairs. I used them in my waders for river salmon fishing.

I used to have a pair. I wore them a lot in the 80s, not out and about, but because I used to do a hell of a lot of stretching as part of my running and found them useful for keeping the muscles warm and supple.

I too would like to master the art of walking gracefully in 12cm stilettos - it’s an acquired skill and I’d like to acquire it, but it terms of simply wearing heels as fashion, I’m not overly concerned about height. I like the 8 to 10cm range and especially chunky or block heels. Whether that constitutes “high” heels is irrelevant to me - and I think probably irrelevant to the world at large, as any guy wearing heels an inch higher than the norm will be considered to be wearing heels, a girly thing to do

My wife used to tell me that shoes were accessories. She chose the shoes that matched or accented the outfit she was wearing. Women’s shoes don’t have to have high heels to look feminine. In her more mature years, she would often wear very girly styles with kitten heels and look smashingly sexy. She often told me that she would leave wearing higher stilettos to me because she found them to be uncomfortable. As for me, I love wearing heels. In my. 30’s and 40’s my normal shoes had 5” heels and I enjoyed occasionally wearing higher heels. Now that I’m enjoying my 60’s, I very rarely wear heels higher than 4” anymore. My main interest has always been “Girls Shoes”, not looking like a girl. But, back on point, you’re evolutionary process is probably normal. Transitioning from pure male appearance to a male wearing female garments in public has elements of your being comfortable at the same time as your overcoming your apprehension about your appearance not being acceptable. It’s a long process. Being a female is a complex process. There is a lot more to think about, especially if you want to appear only slightly feminine. One step at a time!