How to Wear Ankle Booties with Socks - give your jeans 2 little rolls (Madewell Skinny Jeans: Rip & Repair Edition), slip on thicker camp socks (J.Crew), bunch them up, & tuck them under your jeans, slip on ankle booties (Sam Edelman - Lucille in whiskey)
How to bunched socks with booties. Just choose a longer pair of socks so you can pull them over your skinny jeans and then bunch them down. Try wearing gray socks with your black or blue jeans, or pair black socks with your black jeans for a sleeker look.
How to wear ankle booties with jeans / part II: socks!