It's a little stiff when you first try it on, but I have a pair that I've had for 2 years and it has held up beautifully and is so comfortable. This is definitely a shoe that gets better with time. I have ordered two pairs and I'm sad that they stopped making them, they are so much better than flip flops, these boat shoes. It's one of the fashion trends I took from Southern California to Vermont to where I moved! I have so many happy Beach memories that walking around the Green Mountain State dressed like I'm in Southern California does something therapeutic to the soul. These shoes are great, no matter where you live. So much safer than flip-flops and you don't really have to be boating LOL. For what it's worth I have discovered that there are actually several flat espadrilles besides this brand. So I'm not out of luck and will have this style for years to come.