As a commuter, in Chicago no less, I walk a large amount of the day and often on really shoddy sidewalk. Comfortable shoes are a must here, as I can attest to my pile of impulse buy heels I never seem to wear more than once.
Women who wear ugly shoes, such as Toms, who use comfort as an excuse clearly do not know about the plethora of stylish and affordable flats that feel like slippers. I've compiled a list of some styles I've worn and loved and hopefully you can find a pair for your shopping list.
Target's Mieko Comfort Flats
Available in black and dark brown, Target's Meiko flats are a steal. I own these in brown and find myself wearing them with dark brown tights often for a new spin on the black flats/black tights look. They aren't leather, which is good for vegans, and the benefit of this is you don't have to waterproof them if you don't want. I haven't had to break these in at all, pure comfort right out of the box. The sole feels like memory foam with moderate arch support. The soles are also nice and thick, so no worries about feeling uneven sidewalk through your hoofers. My tip, you might want to size down half a size.
Born's Adele Flats
A little more luxe than Target, Born uses high-quality leather on their shoes and you can feel the difference. They might feel a bit tight at first (they are true-to-size), but after a few wears the leather really molds to your foot and they are the perfect size. They have some light padding and great arch support. Make sure you waterproof these, as they are leather. The price tag reflects the quality - they retail for $90 new, but I've gotten this style in silver, cognac, and black from Nordstrom Rack and online retailers in the $50-60 range so do a little Google sleuthing. Born also has some other cute styles of flats, they all seem to fit the same based on what I've tried on:
Naturalizer's Maude Flats
Okay I'm cheating a little here. I have not owned these EXACT shoes, but Target made a knock-off design a year ago and they were extremely comfortable. In fact, they were the gateway to Born's for me. These are made of leather and have a really sleek, yet subtle, design on the front.
And If Nothing Else...Insoles!
Sometimes if I want a wacky color or unique design I can't always get it in a comfort brand. However, if the toe box doesn't squeeze, the heel doesn't rub, and they are inexpensive I can use some of the money I saved on some insoles. Dr. Scholl's makes a wonderful line; memory foam, cushioned, or gel; for the whole foot, just the heel or just arch supports. It's an excellent way to bring your cheap flats into "baby duck" territory.