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Funnily enough only yesterday I bought a pair of boot cut jeans - to wear with my ankle boots with 8cm chunky heels, and because they also look better with hiking boots. Yes, the boot cut partially obscures the heels on my ankle boots, but then I don’t wear them to show off or make a point, and actually the boots looks really good with these jeans.

I decided a long time ago that I look better in slimmer cut jeans/pants. I can pull off skinny jeans, and I like them, but they sure can be a pain in the neck to get on and off. I used to wear boot cut pants all the time for the reason that @Puffer mentioned, as an attempt to minimize attention to my heels, but I guess I got over that some time ago. Because I like to wear mules, I was glad to get rid of boot cut jeans, as the two don't live together in perfect harmony. Perhaps I am mistaken in my self-assessment, because my 40-something woman friend, mentioned several times elsewhere, wears boot cut jeans all the time with 3 inch heels, and she looks awesome. She's a very tiny woman, as well. The downside is, you can't really see the shoes. That was definitely the style in the early 2000s, when she would have come of age. I can remember working at the Iowa State Capitol building in 2004 and watching for heels, which were very common at the time. It was sometimes frustrating, because all you could see was just a sliver of a stiletto sticking out the bottom of a pair of pants that were very nearly dragging the floor. It was against this backdrop that I started my high heel journey, thinking I could do the same.

I am glad you did/do compliment parents for well-behaved children. I remember the first time a restaurant owner approached me and my wife and said something similar. We were taken back because it didn't seem as if our five young daughters (at the time) were doing anything really obedient. But apparently the restaurant had some wild kids in the past. The other day my 19 year old semi-apologized for being bad while growing up, and I told her I did not think our daughters were bad at all. She mentioned a few times we spoke up and stopped some sibling-rivalry but I explained to her that we stopped sibling-squabbling early just so it did not turn into a bigger problem. But growing up... wow! That was over the top. I remember sitting in church and a family-friend asked my dad how us kids were so well behaved and he said, "Oh, I just use a length of garden hose on them". The problem was, that family-friend, teachers and everyone else thought he was joking. My dad had a 4 foot length of old garden hose he liked to wail on us kids with. The real question is: did we turn out good because of it, or despite it? Considering my daughters turned out well so far, and I did not wail on them at all, I think the latter.

When I started to wear knee high, I would hide them under my jeans. Now it skinny jeans and the knee highs on the outside. When you wear with confidence, embarrassment is not an option. And when you wear those boots with leather pants, your confidence is off the chart.

I quite agree! Although I like the look of skinny jeans, I would not expect to pair them with very chunky footwear (not that I normally wear such) nor any with long pointed toes (which I do like to wear). One could easily look somewhat cartoonish with seemingly big/heavy feet (whatever their actual size) sticking out from spindly legs. Boot-cut jeans are (as one would expect) usually a good companion to high-heeled boots, with the advantage of concealing at least part of the heel height if its detection in public wearing would be an embarassment, as many of us have to admit is a concern.