Normally I don't have to break in a pair of Clarks, but these sandals rubbed the smallest toe on my left foot so bad the first day I wore them that I had to put a band aid on. I know eventually this won't be the case and that the leather will soften with time. The fit of the sandal is perfect- I always wear an 8 1/2 medium, and I really like the way they look on. I can wear them on casual work days with jeans- I just hope they break in quickly so my little toe doesn't kill me. Weird, the right shoe didn't rub at all, just the left one on my toe. Still, I'm glad I bought them. Update- 8/5/2016 the sandals have stopped rubbing my toe and are so comfortable to wear now! I didn't have to wear them too much before the shoes started to just slightly soften. The toe thing is something I have to deal with all of the time- I've had both of my small toes broken and reshaped (to a more normal shape), so finding shoes that are comfortable and fit well is big deal, and a big ORDEAL sometimes. Clarks is always my #1 shoe though.