Like Greyscale, sneakers have not been a large part of my wardrobe since I stopped wearing Converse daily. I have two pairs of sneakers that I wear casually, and two pairs that I wear only as gear (one for trails, one for roads). My casual pairs, for now, are both navy. They go with everything. The canvas ones are great for playing around in the woods, on the beach, etc. The slip-ons are great for around-town, and I'm using them as slippers right now, which has pushed their CPW way down. I don't have any uncomfortable sneakers. Converse and I have parted ways for comfort reasons, and though I've tried on a few other trendy styles like Stan Smiths, none of them have been comfortable enough to be worth adding.
Like others, I pretty much stop wearing sneakers altogether sometime in the fall and switch over to boots until sometime in the spring. I wonder if living in a warm climate and having the option to wear sneakers year-round makes them feel less exciting. I definitely prefer the look of sneakers with bare ankles. I think they're much more fun as a warm weather shoe.
I think identifying specific activities that require sneakers and building capsules around those specific shoes is a good way to go if you're finding your sneakers troublesome to style. Also: making sure you have alternatives to sneakers that tick the "comfortable" and "casual" boxes but feel more fab.
