I can't seem to find anything that looks right on me. I mainly wear jeans, straight or skinny, but also want boots that would look good with opaque tights and dresses. I also need to be able to walk in them.
Can anyone give me some pointers so that I don't end up looking frumpy or ridiculously try hard?
I think the current ankle boot trend is not helpful to those who are short/chunky of leg. Anything which chops them off makes them look shorter.
IMHO long boots work better, especially with a heel, and very especially if worn with tights of the same colour as the boot. With jeans it's not such a problem, but I also think it helps if the boots have a bit of bulk to them, from a turnover, straps etc. as it makes it look like the bulk is from the boot not your leg
Slim flats, or dark ankles worn with bare/pale legs not good.