I just bought a pair of Converse sneakers (dark gray, black laces, low top) as a fall/winter alternative to boots once it gets too cold to wear ballet flats barefooted. In addition to jeans and slim pants, I was planning to wear them with opaque tights and dresses/skirts; is this an OK look for dressed-down casual?

FWIW, I'm pretty young--college student on a casual Northeast campus--and the past two years I've happily worn solid gray TOMS with dresses and skirts. But I like the versatility of wearing socks with Cons and they seem a tad warmer than a single layer of canvas.

If the consensus is no, what kind of fall/winter shoe can I substitute? I've been looking for non-black flat oxfords that don't read too old for my age and style, without much luck in a similar ~$50 price range. I do live in boots and booties in the winter, but sometimes an ankle-showing vamp is preferable.