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.