I know this is an old post, but likely an ongoing problem for hikers.

The Keen Targhee's are my choice for backpacking, but if you don't like them, you don't like them. They do have a slightly loose-around-the-ankle feel, but I suspect most ankle-height boots provide only very minimal ankle support. I mean, many people have ankle injuries while wearing heavy hiking boots.

I've tried sneakers once, on an experimental ultralight trip, and they were fine, except crossing a lava flow with loose, fist-sized rocks was a little tedious.

My suggestion is to consider trying a larger size than you think you need. I won't go into my plantar fasciitis rant, as it's probably still on some ancient post, but as a result of having it, I began wearing boots (and shoes)1-1/2 to 2 sizes larger than previously. Sounds weird, and feels a little weird at first, but I won't be going back. Since shoes aren't shaped like feet (though the Keens are better than most), wearing a larger size puts the wide part of your foot in the wide part of the shoe.

Also, try removing the insoles, or try flat insoles. You don't really need arch support unless you have a problem with your arches, and "cushioning" isn't really required either. YMMV of course, but I'm speaking from personal experience and from advice from my podiatrist. There's some good info at his web site: nwfootankle.com. I had a little discomfort at first when I stopped using the Superfeet insoles, but not for long. Keep in mind that the expensive all-leather hiking boots (like I used to wear - Scarpa, Zamberlain, etc.) generally had a flat, thin leather insole. I say "had" because they may have changed. It's been a long time since I've bought any.