I wear jeans with higher socks and sneakers or leather or suede boots in winter. You could also do loafers with warm tall socks.
Your jeans should hit the top of the shoe.

Look at the fall shoe thread - the driving Mocs are made for this.

In warmer weather, I wear straight legged jeans that are the tiniest bit cropped, and wear with shoes ranging from low profile sneakers, ballet flats, and loafers in spring/fall to sandals/birks/flip flops in the summer.

I never know what shoes to wear with jeans in colder weather (late fall/winter). I also don’t know where to have my jeans hemmed to in that weather (I don’t want ankle showing in winter for weather reasons). I’m not into the rugged shoe look and don’t like heels - ideally I’d wear ballet flats or slipper style loafers year round . I like low boots with a kitten heel, but straight legged jeans don’t seem to work with that style?

Please give me some advice.