I have bad feet. I mean, really bad feet. It used to take me forever for me to find a pair of shoes that are attractive AND comfortable. But that was before I discovered Italian Shoemakers. Most of their shoes have fabric uppers, so their soft and incredibly easy to wear. I've never had a pair that needs "breaking in." The styles are trendy and the heels range from flat to high. Many are wedges. The shoes come in some great colors to perk up your footwear wardrobe, and everytime I get a compliment on my shoes, it's on a day when I'm wearing Italian Shoemakers!
Shoes by Italian Shoemakers are also reasonably priced, ranging from about $25 to about $40. I've even ordered them off Ebay.
I don't give them a perfect five because they're not always easy to find. Stein Mart almost always has a large selection of this brand, and Designer Shoe Warehouse, while not having as many as Stein Mart, often still has a good selection.
If you have a problem finding comfortable shoes that are cute and fun, give Italian Shoemakers a try!