I wear walking semi-dress knee-high boots that are lined. It can get cold here in the mountain towns. Last year it was -25 degrees C when we walked around on some trails for 2 hrs. Maybe one day I'll get around to the time consuming search for hiking boots @right price @not too non-blistering.

The multiple shoe thing becomes a somewhat a pain in the butt especially bike touring when we do our own route and self-supported: on some trips I've worn my bike shoes, brought along light running shoes for lots of walking around and the flip flop slippers for showers/hotel rooms, etc.

Running shoes are better for me with a customized orthotic and light hiking.

It's better not to think about the extra weight of bike pannier weight. I gave up on dress or semi-dress shoes...a looooong time ago for vacations.