my gf actually likes riding with one of her heeled boots (heel only about 3/4 inch high) the heel is at exactly right place on her boots so that she can hook the heel behind the pegs and her feet are in perfect position to change gears and use the brake though... She's not home now to give first person accounts but will ask her more when she gets home this afternoon. exactly what aspect of riding with heels concerns you?
Mind you she only enjoys riding with that one pair of boots and no other heels if you have small feet or the heel is at the wrong place you might find that your feet are not in proper place to shift gears and brake I imagine...
[edit] - additionally when I'm not wearing my riding boots (which is very rare) I am wearing my black dress shoes which have soles about half a centimeter high... hang on my riding boots do too... they just tuck behind the pegs when I'm riding and lets me change gears but again, if you can't reach the pegs with the heel or sole tucked behind the pegs you might have trouble.
I have deep pockets. It's just that it's a deep empty pocket...........
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