I don't wear flats a lot, but I do try to mix it up so my ankles aren't stuck in into tip-toe formation. When I do I tend to reach for things like saddle shoes, driving mocs or a newly returned favorite: Cotton Chinese Mary Janes.
I used to wear these quite often a few years ago. They are about $4 a pair and as such they are not very sturdy. But they are really cute under a pair of regular or cropped jeans. And what is great is that they have them in a bunch of colors or even fancier ones in red and black with embroidery. I got the black ones above and the turquoise ones below from Pearl River in NYC.
They have a great website full of clothes, food, stationary and housewares - even these cushy braided straw slippers which are my favorite things to wear around the house in the summer. They are definetly worth checking out.
On the other end of the spectrum from the simple traditional slippers, are the beautifully - almost excessively -embroidered pieces from Perfume River. Their pieces are pricer but when you see the amount of work that goes into them the price will be totally justified. I purchased one of their clutches a few years ago, similar to the one below but with more turquoise versus the coral as shown. This has become my "date night" purse because it is so special and attention-grabbing. But it would be great paired with jeans too.
Traditional designs in new colors and artisan workmanship re-interpereted into modern designs. A few fun ways to incorporate the beauty of global design into your wardrobe and stand out from the everyday.