for me once it hits 50's I am usually wearing a windbreaker and gloves, still wearing shorts though. 40's I will probably be wearing jeans (I only have a 7 mile RT commute) with the windbreaker and maybe a long sleeve t-shirt underneath or a very light fleece. 30's I wear my heavier winter gloves and a heavier jacket but it is still fairly thin, it is one of those ones with the reflective liner on the inside and not much insulation. Below that it does not change much except maybe wool socks and if closer to zero I will throw long underwear on under my jeans.

Short commutes make things very easy, if I had a longer commute I would dress much different.