Help me figure out what casual-but-stylish shoes to wear for an urban winter. Lots of tiresome fashion details inside.
I'm a relatively style-savvy (...er, I hope) woman, but for whatever reason I just *cannot* figure out what kind of casual-yet-stylish shoes to wear now that it's colder. I tend towards cute flats with skinnier jeans in the summer/fall, but that looks sort of stupid with socks, so I'm pretty much trying to find the winter replacement. I'm already a fan of jeans-under-flat-knee-high boots, but I'm looking for something ankle-height, like regular shoes or booties, that I *don't* need to tuck the ends of my jeans into. I'd like either flats or low heels (under 2"), preferably a dark color, leather, under $100 (well, the cheaper the better). It'll be a bonus if it's something I can wear with black tights/leggings and casual skirts, but I really want them primarily for jeans & weekend tops.
I like the cone heel and the toe of these
gorgeous booties a TON, but they're a bit too high and only come in this cognac suede. (Would these look OK with jeans, though? My "skinny" jeans aren't the type that shrink-wrap to your ankles; they're more of a straight-leg opening with "regular" denim that's not like 100% stretch.)
I'm also considering something like this
, even though it's out of my usual look-range and, uh, basically disregards 2 of my 3 criteria above.
Any suggestions? Pictures of people wearing suggested styles would be especially useful--sometimes I like a shoe online, but I can't figure out how it's supposed to work with the rest of the outfit. Thanks, fashionable winter MeFites!