I have a 54cm Cross Check, wear size 10 shoes, and do have toe overlap with fenders on. I got used to it though; it only happens during extreme turns at low speed, so I've learned how to avoid it and it just never happens anymore. I haven't done any loaded touring, but I put a 12-34 cassette on with the stock 36/48 chainrings. It gives me a lot of range without a triple. I just did Cycle Oregon on it and loved it.