Abby - great question! This is a tricky styling situation! As you mentioned, these pants are too wide for tucking into boots....and the weather is too cold to go without socks. (Which I mention only because these pants would look adorable with ballet flats, oxfords or loafers sans socks. Of course.)
So. You want to wear these pants, into the Fall, with warm footwear options. Gotcha.
Now, I don't have a pair of pants exactly like these, but for this tricky styling situation, I didn't want to rely on a Polyvore collage. So I "spoofed" your pants by rolling up a slouchy pair of straight-leg khakis. The color obviously, is different, but I think the overall effect is the same. Here's what worked for me: