In Tokyo the weather usually hovers just around freezing during the winter. I usually wear a Pearl Izumi “heat tech” undershirt with either a Pearl Izumi long sleeve winter jersey, or a light North Face jacket. I don’t like wearing cycling shorts or pants, a well-broken-in Brooks saddle allows me to ride all day in regular shorts or pants. In the winter I usually wear jeans with stretchy fabric. Gloves and a cap which covers my ears is all the rest. It doesn’t really get cold enough to need shoe covers.