Confession: I used to own five pair of Fryes. I now own one, and they aren't boots. Every other pair has been sold due to horrible stabbing pain from wearing, and the saddest betrayal was the Veronica.
They were so pretty, so perfect... so darn painful! I wore them on my last trip to New York and ended up selling them shortly after due to the blisters I received. (I actually wore heels instead for most of my walking which *didn't* cause me nearly the kind of pain those boots did)
Since they've been gone, I haven't found a great replacement. I have those Kmart Doc/Chloe Knockoffs but I really wanted something sleeker for dresses. I happened upon these Mossimo Kena boots while looking for shoes for kiddo at Target and they are fantastic.
Perfect flat boot that looks way more expensive than the $10 I paid for them on clearance. The non-leatherness is a bit off-putting, but for the comfort and style I'm a-okay with it.
Fit on these is true-to-size if you like thick socks with boots. These are the 6.5 and they are wonderful with thinner socks, a little tight if I were to wear thicker socks. I didn't measure the calf-circumference, but it is really forgiving. There are three snaps to change the size of the opening at the calf, and I imagine they would accommodate at least 16". They appear to be out of stock online, but it's definitely worth a trip to your local Target to find them because they are on sale in-store!
Happy New Year!