I love these flip flops! They are super comfortable and a little more dressed up than your regular flip flop. There was no break in for me, they were comfortable right out of the box. They are perfect for running errands in the summer or hanging around on vacation. I bought these right before going to Europe and one had a slight flaw, I contacted customer service and they immediately sent me a new pair. I have been wearing Jack Rogers for years, they are my favorite sandals. Their customer service is excellent as well.