I have a pair of black leather Munro booties that are about to bite the dust. I have taken them to the cobblers multiple times over the last 4 or 5 years, they look okay on the outside, but on the inside are losing their sh*t and aren't as supportive anymore, and no, there's no room for an insole (I've tried). I am looking for a replacement -- have been looking for one for a few years-- and it's seemingly impossible.
I come close, oh so close, but often the booties hit too high on front of the ankle and are too stiff and I feel the shoe hitting my ankle with every step and it's super annoying. The Munro's I have had elastic and soft supple leather and weren't too high. I did not have any break-in time with them at all; they fit good right in the store before I bought them, and that's what I keep looking for.
I like them just high enough they don't show short socks. (I've never met a no-show sock that works for me so don't even bother suggesting).
Or the bootie is just too wide at the ankle and I get that flower pot thing going on and they look sloppy with my inevitably too long pants as I'm short. Heck they look sloppy with ankle pants hemmed just right.
Petty booties are just slightly off for me all around, ankle height, ankle circumference, size etc. Also they feel heavier to me compared to the Munro's. I also don't want a heavy bootie that feels like I'm walking in cement blocks.
I did go on a white bootie hunt and finally settled on the Naturalizer Blair's. These are close to my ideal, I kept them and will wear them, considered duplicating in black. But not as supportive as the Munro's used to be, or Blondo's. The Blondo's are my ideal support wise, I put those on in the store and my feet went ahhhhhh... but the ones I've tried on have that annoying too high/too stiff in the ankle thing going on. Do they make ones with shorter shafts?
Remember I'm just 5'0. Maybe if I was 2-4 inches taller the Blondo's I tried on today, and others, would be perfect.