Which Boots?

My beloved (thrifted) black chelsea boots are slowly dying, so I now have to start searching for a new everyday pair. I've limited my choices down to these exact boots. I know I want something with a wearable heel, but I'm not sure if I should go for the same style of a Chelsea boot, or go for a cutout type. Decisions, Decisions. 

Boots for Fall.

brown boots by candycanecandace featuring high heel boots

Hey you guys sooo, I'm looking into buying a pair of nice ankle boots for the fall time! I've narrowed my choices down to the JC Tardy's (Top left), Chelsea boots(Not the exact ones I want but you guys get the idea), or the brown boots to the bottom left. Which do you guys think is the best? I seriously have no idea. Anyone want to lend me like $500 so I can have these shoes in my closet? Early bday gift maybe? =)