I love the look of a skirt and stompy boots too - but it's really outside my wheelhouse. I would need to keep the rest of the outfit pretty low key to wear it to work. A girl can dream though . . .
Like you, I am always on the hunt for 10 1/2's. I have the Merrells in the non-lace up version in a 10 1/2 and they are very comfortable - but definitely a winter boot.
I have the same problem as you with Frye - and actually with Born too.
10's are too small, 11's too big.
If they have a rounder toe box, I can make them work in a size 10, but any taper and forget about it.
Am following your thread - there are some great options here!