I've been trying for a couple of years without success to find some black boots that I can wear with skirts, that are on the dressy side, and fit my skinny calves as well as possible. Other qualifiers are:
- a low, refined heel
- at least 4 hours of comfort shoes that I can walk and stand in
- not too expensive as I don't live in a climate that calls for boots more than a few months, but when I need them, I really want them.
- not a square toe.
- less than 15.5" tall
I picked out a few possibilities to show you, all on sale right now, and really need your brutally honest opinion. Should I keep any of these or keep looking?
1-4: These are very close to what I think I want. They are AGL Italian leather boots that I found at the Rack. These photos show you what a size 38 or 7.5 looks like with a 14" opening in the shaft. Many boot descriptions say they have a 14" circumference, but that is usually for a size 6. Larger sizes have larger openings. My legs are 12 inches at their widest part. As you can see, even 14" boot shafts are quite roomy. Are they too roomy to look sleek?
Pros: as close as I've come so far to what I want and at a price I'm willing to pay for the right boots. Big enough for light socks and for tucking if I want to. Comfortable enough to be eight hour footwear.
Cons- Even on sale these are still pricey, so I only want to keep them if they are 10s. Do the proportions look right on me? I don't want to buy these and still be looking for my boots.

I'm also considering a bootie instead of a tall boot to wear with tights with a skirt.
The next 2 fit this category:
5-7: Aquatalia by Marvin K., "Versus" lined soft suede leather pull on.
Pros- very comfortable and warm and fit pretty well at the ankle; waterproof; well made
Cons- still expensive; wonder if pulling them on and off will stretch the opening over time; do they look ok on me with skirts or do they look off proportionally?
8-12: (sorry for so many photos but wanted to show several angles). These are Impo "Novice" of all man made materials.
Pros- maybe most fashion forward of the bunch with the pointy toes; dressy; comfortable; ankle fit isn't too bad, less than $60
Cons: not leather, probably won't last more than a few seasons
13 and 15 show Bare Trap shooties that I already own. Will they work as well as any of the others under consideration for now?

Some Sam Edelman "Sutton" sandals on clearance at The Rack. At first I thought that they were "Okalas". Please overlook my non pedicured feet. I don't do polish in the winter in order to let nails have a rest. Are these worth keeping? I like the black with cream snake and could use some black summer footwear, but these are pretty open. They seem very comfortable but need more house testing if they pass your scrutiny. Are they 10s?
I'm really not sure what to do about any of these. What do you think is working, if anything? I am willing to keep looking if that is the best move. I could finish out the winter with what I have and see what next fall or NAS offers. I have a pair of black riding boots with buckles down the side that still have life in them, besides some brown riding boots. As for the sandals, if these are not 10s, I can wait.
Thank you for looking and for any advice you can give me.