I bought a pair of flat over the knee black boots a few years back. I would've preferred knee high, but didn't find any nice ones and these fit just right. 95% of the time I wore them under below the knee dresses so it wasn't even obvious that they were over the knee.
I've just bought a lovely rounded hem dress that falls just below the knee at the longest point. Therefore, there will be no gap in the front, but with walking you will likely catch glimpse of tights on the sides and back. I still feel a bit awkward wearing them, but I think it looks nice?
What about over a pair of nice leggings with a big top? Again, I think this looks "nice" but I don't know if it's dated. Really curious, as I don't see many people with over the knee boots these days.
Just trying to see if these boots still have a place in my wardrobe or if I should let them go. Was hoping to wear this new dress on a trip and the boots seemed like the best option for warmth and comfort.