If you can live with hi-vis: My British police surplus cycling jacket (waterproof, breathable, inexpensive) did well last winter - pretty substantial and much roomier than other cycling jackets I have. On the coldest days I wore a fleece gilet underneath - you probably have that maritime climate in Boston with horrible moisture laden winds, and a cosy extra layer helps. I feel the cold more than most, and never overheated with this setup. An extra advantage for the shorter days is that it is plastered in reflective tape.

Don't all cycling jackets have back pockets? All of mine seem to have whether I want them or not.