These will look marvelous this fall. We usually see a lot of rain in San Jose in the winter so that shouldn't be a problem since these are faux leather (and pretty inexpensive)
These very affordable gray boots from Target look great with jeans or skirts and just in time for the Fall.
Bought these online, and I wasn't sure how they would look in person. They look like leather, even though they aren't, which satisfies any PETA-people :) The top is pretty wide, so they're easy to stuff jeans into, but they look a little too big over leggings or tights. But I can look past that, because they are SOOOOO comfortable! I can walk around campus all day feeling like I was wearing sneakers. Cute, stylish, comfortable, AND cheap.... great deal!