I'm doing this as boots and not as part of the farm wedding guest outfit because I will not be sorted as to tall boots in time for the wedding, but am exploring boots nonetheless.
I just started with an Aquatalia and a Paul Green to see about fit.
Pics 1-3 I have one of each boot on! PG is on my R foot (L in photo) and Aqua on the other.
The PG is suede which can be forgiving. But, the front bit comes up over my patellar tendon just enough to bother me--maybe it doesn't look so, but it kinda evokes OTK and also I can feel it when I walk. So they're a tad too tall. Fit is fair and toes are pretty comfy, but not as cushiony as I'd like and not much room for an insert. 
The Aqualltalias are a good height but are the slightly pointy style of this year. They are pretty forgiving in the bunion area but it's not ideal for me to invest in the pointiness.
I showed first pics with sheer nude hose so the boots would show better, but I'd probably almost always wear dark sheer or dark opaque hose.
Next pics are just the Aqua's (on both feet!) with  skirt I'd wear with tall boots and a dress. 
I AM learning something about boots.First, I'm not a super tall-boots person. I don't so far think they are as comfortable as warm tights and a lower boot or oxford. But, I believe I would mostly wear with skirts or dresses that are fall-wintry. I So a fitted style is better than one that allows tucking in pants. A low heel is best for my feet and also so I'd wear them for "dressy casual" or sporty dress and get use besides work, like a dress and fun vest, or tunic and tights. I think a water -resistant type would be good since it's a way to wear something on a chilly rainy day--not for hiking in rain, but dashing in and out, boots and warm skirt/dress-trenchcoat kind of thing.
So probably a smooth leather, low heel, water "proof", refined but not too dressy. Does the riding boot strap & buckle make boots too casual for a skirt? Or is it more the overall cut and effect?

I'd like a toe that's less pointy than the Aquatalia  one, but not bulbous!
I expect black would be most useful. I would love various browns for leather, but statistically black would be easier to coordinate with likely clothing colors that come and go. For example, can still wear black with navy, or can wear black boots with warm camel type woolen skirts or dresses.
But, are all the boots made with the whole back as fabric? I can see how that makes for a much better stretchy fit, but it seems like buying half a pair of boots!

New question if anyone can weigh in: I was rethinking what works or not re: the Aquatalias. The calf fit is pretty tight at the widest part of my calf on though the stretchy panel keeps it from being a real problem. BUT the boot leather does some of that “buckling “ right above the ankle. I note when unzipped, of course, tgevkeatgrr rekaxez and straitens out. Does a tight calf cause more wrinkles and is that some kind of happy medium to look for? I’m not bothered just by appearance but whether over time the leather wears badly in the wrinkles. How “ smooth” should s boot fit in that zone?
Thanks for any feedback.

This post has 5 photos. Photos uploaded by this member are only visible to other logged in members.

If you aren't a member, but would like to participate, please consider signing up. It only takes a minute and we'd love to have you.