Chimney Shoe Question

Wear something comfortable and with a rubber sole. I've had luck with the "Skater" type shoes they are made to grip the surface of a skateboard. You can find them cheap and they do a good job of gripping the roof. I've also found that a lot of work boots don't hold up that well on the roof and tend to not be as comfortable. But most important find something that feels good to you and maybe do a test run on a shallower roof to get a good idea on how they will perform.

soft rubber sole is best. cold or wet can make soul slippery

Yes, please stay off a wet roof.

While I was doing my mid-winter check of my liner it started snowing, by the time I put the cap back on the roof was already getting covered in snow, that was the scariest experience I have ever had. I always just wear my tennis shoes, but with the pitch of my roof my ankles are killing me from standing at the peak while cleaning my liner, thinking I might try my boots the next time for ankle support.