It doesn't matter how often you wear heels, or how often you claim how "comfortable" they are, the flip-flop is the comfort-food of footwear. It's easy, low-key, and the closest thing to walking around barefoot (yet without the hillbilly factor). My hands-down, tried-and-true favorite is the brazilian brand Havaianas. Those Brazilians know their sandals.
These flip flops are sturdier than your standard pair, hold up for an entire summer (even with everday wear), and best of all: no toe chafing! This is a biggie for me concidering every other pair seem to rub in that spot between the big toe and the other toes. Concidering the generally cheap price of other flip-flops, these may seem like a pricey pair ($15), yet they are worth the money for the comfort and the ease (not to mention the fantasy of that perfect Brazilian cabana on the beach that I seem to daydream about whenever I wear them!)