I have begun my annual quest for almost-flats that are both comfy and cute (and fit a few other criteria). I just don't wear flats in the Winter-time very much, I think of them as a spring/summer thing...I guess the "ease" of them seems Summery.
I used to be (as many of you probably also were) a devotee of the great $7 China-flat, but the lack of any support and their tendency to look disgusting quickly has made me increasingly look elsewhere for the past few years. That's not to say if I found a black pair that was wide enough for my hobbit feet I wouldn't snap them up, but right now I'm looking for some considerably "real"-er shoes.
I found these yesterday whilst poking around Zappos:
They're from Ecco, surprisingly...they're so sleek and elegant to me.
They also fit an important criteria for 99.9% of flats: they have a mary-jane strap...important not only for the cute-factor, but for the more vital "these-will-actually-stay-on-my-feet" factor.
I also ran across this pair of slightly-chunkier and more elfin shoes, that my pal Sara happens to own (so I can attest they are so very cute in real-life, too):
These are made by Clarks (again, so much cuter than you'd expect from the brand!)
I think I'm going to go with the Ecco's...but the problem now is whether to get red or grey? I love the idea of a grey shoe, and they're very hard to come by...but red is like my neutral.
Hrrm. Maybe both.