Converse All-Stars have been around since 1912, and since then, their design has not changed that much. While there are more models and high tops available, there have only been minor improvements. One would think the flat sole and lack of foot control contribute to an uncomfortable shoe, and yet they continue to remain a staple in the eyes of sneakerheads everywhere. The lack of arch support, however, is something to consider for flat-footed people. They were initially intended for basketball, aka short-term use, so wearing them all day was never really considered in their making. So to answer the question: are Converse sneakers comfortable? It tends to be different person-to-person. If you need a bit of support, these are not ideal for all-day wear unless you use a sport-insole with built-in arch support. However, for people most comfortable in a flat shoe, these are the ideal, durable choice.
Your best bet is to try them out for yourself. Test your Converse sneakers in Toronto and enter to win a $50 gift card.