I don't think there is anything as chic as a smart pair of flats.
Here are some recent items of lust and/or disgust via a Zappos round up:
Gorgeous Sigerson Morrison nude patent leather with gunmetal beads. I've been on the hunt recently for a pair of camel flats to match the camel tote bag i've been sporting (an amazing thrift store find with Marisa in the Haight in SF over Thanksgiving). These are probably too fancy to match the aesthetic of the beat up tote, but they are beautiful. Down to $248 from $444 on zappos.com. Still not exactly recession pricing. It makes me sad that the almost across-the-board beautifully designed S.M. flats are still not affordable, even on discount websites. Wah wahh.
I'd like these Kate Spade moccasins a lot better if they didn't have that dumb bow.
I've been eyeing these Dolce & Gabbana violet flats for a while. Can't decide if I love them or hate them. I tend to think Dolce is kind of trashytrash looking, but I like the punchyness of these.
I know I just trash talked the Kate Spade bow, but I pretty much love the proportion of bow-to-shoe on these Tapeet flats. I never could resist a fuschia shoe (I may or may not be wearing some as we speak). But I would like them better if they weren't cut outs.
LOVE these Elie Taharis. Really would like a pair. They come in lots o' colors, as well as in a patent finish, but I really dig the gray suede.
And finally, these heinous Marc Jacobs. These are not whimsical, these are some rubber fugness that really disturb me.