I'm not sure how much ankle-panting I will be doing this summer because it's kind of a fraught, leg-shortening look for me, and also, it's chilly for air-conditioning. So it is not an all-in look for me, more of a dabble!

But, I have sort of figured out that the way I like to do the shorter lengths is with some gap-closure from a higher shaft footwear like a bootie, OR from the high ankle-strap footwear. I was so surprised at how well I liked the ankle strap--because I had thought of them as leg-shortening, as they appear when worn with skirts and dresses. But with cropped pants, they have the opposite effect (thank you, Angie).

Along with this is the amount of pants taper. More taper can work with some loafers, but if the pants are a little wider, or slim-straight, I'm not keen on the straight pant, the bare leg and then a shoe at the end of it (for me). So all of these things do depend on proportions.

Last summer I had some fun with ankle-strap sandals that will continue to work well with casual ankle or cropped or rolled pants, but I cannot do open toes for work.

Therefore, I'm doing some not-yet-intense investigating of whether there is a closed toe, comfortable option with an ankle strap, or a summer boot, or maybe a ghillie-tie or something, in case I want to do an ankle pant but with a gap-closing type of footwear.

In the Find is a rather casual EF sandal, but it gives an idea of what might work. I tried the Allot flat, that Joy has, last year, but they don't fit me well; otherwise that would be a nice option.
I'm also leery of the very pointy-toe versions.They look great, but the comfort level breaks down. I have a more refined version I got to wear with a dress to a wedding, but don't think it works for all-day wear.

Some kind of open-cutwork bootie might also work. Actually I guess one could just wear regular ankle boots, revived by the "breezier" vibe of ankle pant for summer, but sometimes the fall-winter boot just does not look right out of season. Probably not as much so with lighter colors, taupe, beige, but then these don't bookend as well for me.
I like the idea of a small bit of heel to add length, but at the risk of sounding very conservative, there is something about a heel, even chunky, and major ankle-exposing pant, that can read too "prancy" for my goals for my workwear, whereas I would wear that out to dinner or for smart casual for sure. A more clearly "action -ready" shoe actually reads better.

Is anyone else working on what type of workplace-acceptable, summer footwear for ankle pants AND comfort? Or are you planning to continue your boot looks across seasons?