You'l.l need to layer.  It is probably easier to buy boots and a good coat when you arrive in Canada.  Jeans are fine but not great if you are planning on doing things outside like sports s you may want to bring a pair of sweat pants/athletic pants.  You may want to buy long underwear to wear underneath.  Same as tops you should dress in layers like undershirt, long sleeve shirt, sweater/sweatshirt and the jacket.  Hats, scarf and gloves/mitts are needed.  It can also get very warm in summer.  Between 30-35C plus humidity so you also need summer clothing.  Don't worry the weather in Windsor is mild compared to many cities in Canada.