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Humectants shouldn't be used in cold and dry weather, because they draw moisture from their surroundings. They're good for when the weather is humid, because they essentially keep moisturizing your hair throughout the day by pulling the water from the air. But in cold and dry weather, they only dry out your hair. There's no moisture in the air for them to eat, so they take it from your hair instead. To lock moisture in the hair during the colder months, I find that for my hair, it's better to use something oily and thick....I like castor oil, sunflower butter, or avocado butter.
I think you're right about the silicones though. I use them all year round though, I don't care.