I like to wear the same shoes for everything, so I wear Merrels that are a typical light hiker/trail runner style shoe. I suppose the tread isn't the best for the Sylvan style pedals. The All City pedals pictured above appear to have larger teeth than the Sylvans, but don't seem to make much difference. I understand that they'd work much better with toe clips as the first poster mentioned, but I chose to stop doing that years ago. Maybe it was dumb of me to think they'd work well without the clips.