I used to have a U-shaped commute. In winter I would start downhill and cold, then finish overheating on a 15% climb. I took to wearing a fleece gillet over my windproof and removed it for the climb.
in a very similar position, live at the top of one big hill, work at the top of another and have to go down into a valley between.
Start off with numb fingers and tears freezing on my face, end up glowing and dewy!
One of the main reasons I like to have a basket in the front is for the ease of chucking in my layers as I strip off en route!