The Sperry Top-Sider, being around since 1935 and still being worn today by so many I would say definitely makes them classic. Ranging in all different colors and styles they can be worn with just about everything. There are so many other brands now, doing different spins on them. I just bought a navy blue pair from Dexter. Here are a few others:
I know this was a blog on boat shoes...but while looking at some online I came across these Kate Spade wedges and automatically fell in love with them...had to share!