I found this shoe to be too large - I wear a 7 usually (in Chacos, also), and ordered a 7 in these shoes. I found them just a bit too big. I have worn them anyway (I had to cinch the straps pretty tight, which stretches the elastic near the buckle). I would not really recommend them for walking on uneven surfaces. I took them with me on a trip to Vietnam, and while walking around Hanoi I nearly turned my ankle several times because the shoe slipped out from under me. For a pretty expensive pair of shoes, I'd like stability and fit. I didn't return them because I live in China, and just couldn't. That was my risk to take, but I would have returned them if it was easier. I wear them for even surfaces and easy walking, and they look professional (and cute) enough for the classroom (I'm a teacher) but they're a little disappointing for Chacos.