I too have a problem with losing one toe nail each year. I was told I need lots of toe room in my shoes, so I got new shoes - lots of toe room, but still lost the nail. I am going to try toe covers this year, they are clear silicone covers that go over the toe(s) and cushion it. You can get them at the Running Room etc. I've also been told by my podiatrist to tape the "offending" toe to the one beside it, stops it from bending and getting bruised while walking. I will try that as well this year. For me it just seems inevitable that I will lose at least one toe nail a year.
I've thought about walking in my Birks - and will be bringing them this year just in case. Try everything you never know what will end up working out for you.
I lost one toenail on each foot the first year, but never since. I wear shoes with lots of room in the toe box (up half a size over normal), and cut my toe nails VERY short.