Yesterday, I did a big pants/jeans hunt at our local boutiques. Bought nothing yet, but want to run ideas by you all.
One boutique has Lysse, which work well for me cause they're pull on (non negotiable with my weight fluctuations), high enough rise in back, and their indigo rinse is a bit greenish which I prefer.

Currently I have by them indigo bootcuts (best jeans Ever) and brown wide legs, which are ok but shorter than ideal with heels for my taste. The brown ones are passable as regular pants for the office, indigo maybe ok to work Friday and Saturday, but I save them for days off.

I tried on 3 contenders in store, and checked Nordstrom online for their options as well.
1. Bootcuts with a front slit, indigo. They're basically identical to the ones I love, but for the slit. A quick styling search just showed the style with sandals or pumps. Would ankle booties look ok if shorter than slit? I had short snow booties on yesterday and it was a bit odd.
2. Slim straights (I'd call them skinnies), indigo with thin tan piping on side. Didn't love with the snow booties but maybe ok with normal booties? Tall flat boots would be ideal, but my only ones are snowboots. They could feel less "splitting my wears" than #1.
3. Wide leg medium wash. The color felt too light and cool, but could order in indigo. Shoe wise they're easiest as I wear ankle booties all winter, and could be better with sneakers than the others.
Maybe passable for work too in indigo?

Most of you have multiple pairs of jeans, but I haven't in a long time. Since I've been working part time, and am doing errands all my days off, I feel like I can justify another pair. Just trying to decide what's most useful, easiest to pair with my shoes, smart casual instead of very casual, and won't feel dated next year.

ETA- if you have multiple pairs or jeans, do you treat them sort of interchangably, or for different types of occasions?