Being in my 5th year of bicycling trips, I have a pretty good idea of what has held up over time, and what I've had to replace.
Shoes: My bike shoes are still in really good shape, and I don't wear them as much as I'd like to. They still have 8,000 miles in them. I'll come back and edit with brand and pictures, all I remember is I got them at REI. They're recessed MTB clips, so I can walk around in them fairly easy. I debated switching out to flat pedals for this trip, but I'm pretty good about clipping out quickly with the kids' sudden stops. My only hesitation is the mud that gets packed up in them.
Off the bike shoes: For the past 5 years I've had a pair of ballet-flat crocs, and they have all the benefits of crocs: they weigh nothing, they pack anywhere, they can be washed off. They also have all the downsides of crocs: feet sweat, no traction, and I've pretty much worn through the bottoms at the ball of my foot. They've gotten a lot of year-round wear over the past 5 years, and it's time to retire them this trip. For $24, I got my money's worth. If I weren't sightseeing as much, I might get another pair. They make great camp shoes because they're closed toe and ultralight. And, the ballet flats aren't ugly.
So, I upgraded to some knock-off Keens I got at Big 5 Sporting Goods. On sale, they were $16. Mom went to go take a look for a pair and she could only find them for $59. If they were full price, I'd get the Keens, but like Bryan's shoes, it was a last minute find. "Outland river shoes" have the elastic bungee straps and the toe protection. Unlike the crocs, I feel like I could easily pedal in these if needed.
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