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:
If the combat boot is too literal, you could try a short bootie. It's just as cool, without the military feel. The small (yet comfortable) heel helps keep the look feminine.
Sock color - there are a couple of options. You can always match the socks to either the pants or to the shoe...but I'm loving the look of socks peeking out. So I choose a contrasting color that would stand out.
Because duck boots are so preppy, I think they'd provide a cool balance with a some military inspired cargos. Not to mention that this is the most practical choice, especially for cruddy weather. I do love my duck boots. Wore these babies all winter last year.
(wearing: Gap turtleneck sweater and khakis, Lands' End Duck Boots)
Slide Tall Boots Under....
If you have a pair of tall boots that are slim, you might be able to slide them underneath your cargos...and just roll the cargos just a touch. This look can get very Dickensonian, though, so watch what tops you pair with it. Personally, I'd avoid ye olde time waiste-coats and cravats.
(wearing: On S - Gap khakis, J. Crew cotton moto sweater, Free People crinkle tunic tank, Biviel tall wedge boots.....on P - Imps & Elves striped pants, Target long sleeve tee)
So that's what worked for me...but our readers are always full of fabulous ideas. Readers!! Do any of you have pants like Abby's? How do you wear them in cold weather?
Thanks for writing in, Abby!