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Layers for sure. We offer branded fleece sweaters for our staff to wear over their uniform shirts (they purchase) and we encourage they wear layers and also bring a change of clothing for the ride home incase they get wet. Staff who work outside will definately require a good set of boots and outerwear. On days where it is exceptionally cold, we allow our staff to wear additional winter clothing as long as it is black in colour.
I've been wearing ECCO Track II Mens Casual Hiking Boots GORE-TEX WATERPROOF Brown Leather like these for years.
Best boot I've ever worn for winter climate.