How do you dress when wearing ankle-length rain boots?

I find long boots a bit too much of a hassle, so I usually wear regular ankle-length rain boots, but I just can't seem to give up wearing rain boots on rainy days. However, wearing shorts feels a bit awkward, so I just put on straight-leg slacks and wore the boots. For those of you who wear ankle-length boots, what do you usually wear on the bottom?

Whenever I wear regular straight-leg jeans or pants with even a slight jogger fit, I end up looking a bit like a fish market style lol. I need to wear boots, but I also have to worry about my outfit ^^; Please let me know if you have any tips or recommendations.