Catnap,
I don't know if you are thinking about getting clipless pedals and shoes yet, but I would recommend it. The soles on cycling shoes are made stiff so that, not only does most of your pedaling power goes towards moving you along the road or trail, but it evens out the pressure on your feet. Sneakers are okay for short rides, but really don't work well for anything extended. They just don't have the support you need to pedal. I used to have numb toes all summer that lasted till about Christmas time. By then I had been off the bike enough that the toes recovered. That was using toe clips and stiff-soled bike shoes. Once I switched to clipless pedals and cleats, I never had the problem again. There aren't many cycling shoes made solely for riding with toe clips anymore........ you can use the ones made for clipless systems, I guess. I don't know how well they'd fit, not having done it, but I think it would work. Then when you were ready, you could switch pedals and you'd be set. Or just go with the pedals and shoes to begin with and be done with it, if your budget can handle that. You can watch for sales. This is a good time of year to find shoes on sale. The shops need to make room for new stuff.
Good luck.
Time is a companion that goes with us on a journey. It reminds us to cherish each moment, because it will never come again. What we leave behind is not as important as how we have lived." Captain Jean Luc Picard