i am all about the pirate-y / puss-in-boots look. i think it would look great with tucked in jeans, cropped pants, and a slightly full skirt. also i think the detail of bright colored tights will be really cute.
with this pair, i wonder if you can flip the top up?
Those are gorgeous! dot had great suggestions on pairing them with outfits. Also check the lookbook at shopbop.com, they have a few outfits with pirate boots.
i love the look of those boots. i actually have my SA at Nordstroms on the lookout for when a pair of Miss Sixty's get in. they are similiar to the Aldo ones you posted but with less of a flap.
i was planning on wearing my with my jeans tucked in, gauchos and skirts. so i guess the same way dot has them planned for you!!!! and i agree that shopbop.com has some great ideas as well. that is actually where i first got the desire to purchase a pair of them!