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I’m just back from a stroll to the supermarket, a mile or so each way, and with the supermarket being in quite a busy crossroads, and at quite a busy time - lunch hour. I wore my grey suede OTK boots, medium heels. Usually I don’t bother noticing if anyone is noticing because I don’t care, but today as an experiment I decided to look at where people hold their eyes when they are out and about. In almost every case it is straight ahead into the vague middle distance, or else they are looking for something, or speaking to someone. In any case their observation threshold doesn’t appear to be lower than the waist. There are those of course with downcast eyes, either gloomy or lost in thought or because they are very introspective. And again, these people don’t seem to observe much either. One woman noticed my boots - she had been gazing at a spot on the footpath and I happened to walk through it. She glanced up at me, then back at the boots and then returned to her own private bubble. Now I was wearing, as I said, mid-grey suede OTK boots paired with fairly light coloured, but not pale, blue jeans. And worn outside the jeans. They worked together in a complementary way. If I had been wearing something more eye-catching - patent thigh-highs - maybe more people might have noticed. The point is that while we may be conscious that we are wearing something outside the norm, most of the rest of the world just doesn’t. Especially if you don’t make a show of it. I mention this because of some posts I saw lately where people were wearing really quite presentable boots and were nervous about the reactions. Don’t be. It’s fine.

You do come across as you intend - a regular Joe who wears heels in a classic way. A great advertisement for the style

Although I have mostly size 10 some 11 (US women's) feet, I have strange pear shape feet. Large thick toe box, skinny heel. For too many decades I suffered through men's shoes, 9.5 EEE. I could get my toe box in but then have over 1 cm gap on each side of the heel. This lead to multiple ankle problems, injuries, and surgeries. This issue stopped when I "discovered" women's shoes fit my feet. I went from hating shoe shopping and having few shoes to enjoying shoe shopping and having over 80 heels.

I always wear mine over my jeans. I like the look and also, in the case of OTK boots it’s just way too much of a hassle to do anything else. My boots are fairly conservative in style - classics, real leather or Nubuck suede, and quiet colours which pair well with jeans. There’s no reason for them to attract attention

Great feelings indeed, the best! Thanks for all your encouragement buddy, I have finally mustered the courage/confidence to properly wear my boots over the levis. Actual comments/compliments are rare, but sometimes I can almost "feel the stares" as if folks were talking out loud. I'm always nervous about being around kids, especially in tight places such as elevators. We all know that kids have no "filters", and will say whatever is on their mind. I can honestly say that I have never actually heard a little kid making a comment though. Every once in a while, I do get a compliment, split 50-50 between women and men. Most are too polite to make any negative comments, although I am sure there are comments after I have passed by. I try to remember that the most negative comments usually come from the most frustrated, whether it be women or men. At the end of the day, I must remember that I think I look great in boots, which is really all that matters, although I'm not afraid to admit that I value and appreciate positive feedback from others.

I wear my boots on the outside of my pants all the time. The last time I wore my Jessica Simpson stilettoes shoe shopping, the shoe manager told me she had the same pair, but had to give them away when her feet grow during pregancy. Mine are not "modest" heels, most 4 inch + whatever platforms. I get the eye roll, more often from older adult women. The eye roll is where they see your boots, roll their eyes up and see you're male, then roll their eyes down to look at the boots again. By that time I am past them Kids sometimes will point it out to their parents. Rarely a comment. My boots are real or faux leather or suede. I would guess the responce might be different if I wore a fetish or shiny plastic looking boots. Or boots covered in sequins. It took sometime to start wearing them on the outside. But my boots weren't cheap, so why hide them. I trying to expand my boots into other colors and styles, like the western boots in ICE from Freebird.