Main Motorcycle: 2014 Scram "The Crow"
Join Date: Aug 2011
Location: Vancouver Island, British Columbia, Canada
Other Motorcycle: Former - 2010 T'bird
I go for the big engineer boots that you can get cheap from RiverRoad or others. Less than $100 and last a long time. Wool socks in winter, cotton in summer. Ride all year round in Canada and not a problem.
For the jacket, I have a number of them. For pure comfort and warm/dry you can't beat the Triumph adventure lineup.
However, I prefer leather. I have a custom fitted jacket from Bristol Leather. It has a liner. In the summer I take the liner out. In the winter I keep it in and add my electric heated Gerbing jacket liner.
The Gerbing heated gear is awesome. You can wear your leather in mid winter and feel great.
I've never had much problem with leather even in hot summers riding in the US. Just make sure your jacket has lots of vent zippers and like others have mentioned, removable liners and layers is what you need.
However, I do not ride with a windscreen. When I've ridden bikes with a windscreen I have been unbearably hot in the summer. Lots of airflow is critical in summer.
What if there were no hypothetical questions?