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I had a gorgeous pair in high heels in 1982. Wore them to a job interview as a teacher in a secondary school and got it - Male head teacher. I looked very elegant in them, nothing like a pirate <preens>
I have some flat black suede ones from R&B and absolutely love them. Have had them for years but they are twice the price now. Mainly wear with skirts/dresses - don't tuck things in them. I'm a size 8.5 and 5'9".
Made me laugh " hooker". Never seen mid thigh boots, but suppose no point in wearing them to hide, so would have to be worn with a tiny mini skirt - definately a hooker look !! If worn over thick tights/jeggings, would look more like going fishing, especially if worn with a long jumper to cover bum and thighs.
I bought some flat over the knee boots in black (faux) leather a couple of years ago, wear with leggings, jeggings, all length of skirts, and have almost worn them to death – shopping, work, church, everywhere. No adverse comments at all.
I was thinking your dress or skirt would have to be very short to wear with thigh high boots too. I'm getting a totally different picture about knee length boots which I do think look good. Thigh high ones I think would be more limiting.
The 5050's mentioned down thread are the ones. But exxy. Mine are dead now but lasted years. I'm about 5'9" and they are quite high though even on me. A little limiting. Bear structure in mind too. Most will head a bit south over the years.
These are the ones mentioned earlier Honeycrest. They are really nice although exxy of course. Mine did last for years and took quite a long time to become just a bit loose. But they were worn to death. I have in the end bought some Dune ones just a few weeks (but brown suede rather the black leather I had previously). The Dune ones are nice and were 75 quid in the sale. No comparison pricewise. They are much thinner and actually seem much shorter . In fact although I expected then to be over the knee, in fact they are not really. But I like them and in fact they are somewhat more wearable than the 5050's as a result.