Did you already solve this? That is rather broad question. 

setting up odoo is one thing and setting up a proxy with ssl another.

If you got odoo working then in my opinion easiest is to install nginx for windows if you really are dead set on using windows. its fairly straight forward to configure and there is many guides to doing this. so basicly when someone opens your odoo site nginx fetches the data from your odoo instance on port 8069 (preferably on local host) and then encrypts the data using the certificate and sends it back to the user over https. 

user proxy with ssl odoo

Probibly there is many other ways to solve this also but im not a windows guy so this is the best i can do. hope it helps