Ok, I am a boat shoe fanatic. I've had pretty much every brand and tons of styles. These are considered the milestone or the archetype boat shoe. I will say that these AO's are probably the most comfortable, right out of the box I've ever seen for a leather boat shoe. The sole is super flexible and the leather is soft and flexible. You can easily wear these without socks too - since they're leather lined (which is getting harder to find now). They look great and I happened to get this pair for $69 - a super good deal. At the normal price of close to $100, I don't think it's worth it any longer. I also have a pair of Sebago Docksides and I think they feel a lot heavier and longer lasting. If you want a super comfortable boat shoe, get these. If you want more of an old school, longer lasting boat shoe that's leather lined, I'd get the Sebago Docksides. Personally, I like having them both. These are more comfortable, but will not last as long as my Docksiders. I could wear these all day with or without socks and be fine. Overall, I'm happy with my purchase and would likely get another pair. I may try LL Bean Casco Bay boat shoes though - I've heard good things about them.