I got an urge to buy the old-school Eastland mocs I wore in Junior High, but in looking for them I stumbled across the Overdrive Ankle Boot and fell in love. I went for these instead and I couldn't be happier. They're very comfortable and aside from wearing them on the pavement to scuff the soles so they didn't do that awful new-shoe-squeak on linoleum floors at work, they didn't even need breaking in. I wear them with everything - jeans, casual dresses/skirts, shorts. To me they're a classic look and I suspect I'm going to get a lot of years of wear out of these.