You may want to pack light because airline luggage restrictions are tight. For winter, you need your warmest clothes, in many layers, and waterproof boots. A scarf that covers your face is a good idea—winds can be brutal. In summer, loose-fitting, casual clothing will see you through both day and evening events. It's a good idea to pack a sweater or shawl for cool evenings or restaurants that run their air conditioners full blast. Men will need a jacket and tie for the better restaurants and many of the nightspots. Jeans are as popular in Toronto as they are elsewhere and are perfectly acceptable for sightseeing and informal dining. Be sure to bring comfortable walking shoes. Consider packing a bathing suit for your hotel pool and a small umbrella.