Thanks for the responses everyone. These suggestions are helpful.
jCrew usually does not quite fit me but perhaps I need to give them a second chance. As for my budget, I'm looking to spend no more than $350 if possible but if it's simple, and perfect, I'm willing to be flexible!
I am looking for something simple and without such a big heel. A lot of boots these days seem to be around 4" and I'm looking for something more around 3". If anyone knows of a brand that sells an ankle boot with this heel height, and a more rounded toe, any suggestions would be greatly appreciated.