I am trying straight leg pants( not jeans) over a dressy or sassy loafer-- like your Kate Spade. Low enough vamp to show some top of foot, but scrunched a little. I'm trying not to build too much around pointy toes, which are not as good for my foot health, for regular work days.

It's a fine line we walk between frumpdom and stylish but foot healthy, isn't it? I had a try-on session this morning with what I have in my closet. I agree with you that a low-vamp loafer with a slim slack with some scrunch definitely works. I still struggle with jeans though. Stuck in my head is the thought that pointy toes make jeans (on a short person!) more work appropriate. Yet, I didn't really like them with the shoes I have. I ordered a pair of booties to try, but since fit is so crucial for me, I'm not holding out much hope. Still working on it!