I have been having an internal debate since Lisa posted the burgundy boots from Little Burgundy. I have a fairly significant selection of boots and added 3 tall pairs and an ankle pair already this season. Plus I bought a pair of doc martens that I gave to my niece. I wear boots almost daily in fall/winter but have a tendency to overbuy and then wear a favorite to death.

I wore booties a lot last winter and have given away a few this year already. So far, the only pair I have worn are forest green booties that are super comfortable but may not work well with the faux leather jeggings/ponte pants.

I have been wearing the new black booties at least two times per week since I got them so perhaps a similar style in terms of shaft and heel height would add variety rather than splitting wears and burgundy is a good semi-neutral with the greys and blacks.

I added finds for the two that I am wearing now. I can't figure out if I am being a lemming or need another pair of taller ankle boots in my life. How do sort through this type of dilemna?