I own 2 pair of Crocs women's Freesail and figured I'd try a pair of the classics. The Freesail are much trimmer & narrower in width than the women's Classics. I love both. The Classics are quite a bit boxier and wider in width than the Freesail and the Classics seem to have a bit more cushioning on the bottom. Both work well for my problem feet which are usually sporting the Alegria brand shoes/sandals for work. However, on weekends and downtime, I prefer Crocs. I have hammer toes and deteriorating foot joints and have lost most of natural cushioning on the bottom of my feet making it feel like I'm walking on marbles. I typically wear a women's 8/12 or a European size 39. In Crocs, I always go a size 9 for the length. I love both the Freesail and Classics and would urge anyone with "touchy feet" to give these a try.