Aka- why isn't it summer year round?

Sooo, I'm trying to get my cold weather shopping sorted, or at least firmly in progress early, cause it's So Darn Hard :/

I tried on the cropped jeans with my ankle booties, and they looked really awkward. Several inches of skin between boot and jeans- not what I'm going for. My tall boots are buried in my cedar chest, so didn't try them yet. They work best with sandals, but not much weather for that. Late Oct-November and April I'd wear pants + sandals. So so with loafers and mules- which probably can work through December in my climate. Store pics show similar with sneakers (too casual for my comfort), sky high pumps (also no) and sky high nude type sandals (nope).

Then I picked up some fairly slim cut work pants, ankle length, with a small slit on the side. Great with loafers and mules, and sandals of course. But odd with booties cause the slit...my sock booties maaaaybe, the other 2 no. Maybe they will fit under tall boots?

To be practical, I really need all my pants workable in the 30-70 degree range.

Wdyw (work/smart casual) with pants/jeans like this?

ETA was looking at Angie's outfits and she had a lot of boots ending right where pants end or pants scrunched over a bit. The work pants aren't long enough to scrunch over, they just kinda sit there.