Black Booties I've tried this month:

 Marc by Marc Jacobs. Suede & Shearling Wedge Ankle Boots. $320.00. Size 5.

Returned: Reason: Too expensive and slid off my narrow heels. It looks gorgeous though.

Nine West Tulley Ankle Boot. Size 5.
Returned: For the price, the quality could be better but they are very comfortable.  

indigo by Clarks Mckenzie Faith Ankle Boot
Kept!  Reason:  Overall, very cute and comfortable for a night out for dinner/bar.  Runs small.  I'm usually a size 5 but these I had to order in 5.5.  Kept the size 5.5!  Bought Miu Miu boots~ and kept those instead.

Aerosoles Plum Luck Boot bought from Outlet. Size 5.5
Kept! Reason: Comfortable, affordable, and cute!  My favorite out of the bunch.
Heels are 3 inches.  Bought the 5.5 because 5 wasn't available.

Nine West  Realmo from Outlet. Size 5.
Unsure: Reason: I bought this for work.  Heels are 3 inches.  The back feels a little loose.   It's still comfortable, but I don't know if it would bother me later.