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as others said: make sure your core, head and neck are sufficiently covered first. merino baselayer, decent mid-layer, windbreaking out layer, merino gaiter, merino cap.
in my experience, you either buy winter shoes or you deal with the pain of putting on overshoes and such. i.e. winter shoes generally don't extend the range of ride-able temps (or at least not by a ton), they just make the hassle of getting dressed slightly easier. I like the Rapha deep winter overshoes a lot, but mainly because I got them on sale; there's similar stuff out there. when it's sub-freezing, I put a chemical warmer over my toes, over my shoe; i.e. *between* shoe and overshoe. and then I wear a medium-thick wool sock (I like the Chrome ones) and am careful not to cinch the shoes too tightly, which constricts blood flow. make sure you tape over any vents on the bottom of your shoes.
gloves, I like Rapha winter ones down to 40 and Castelli Estremo below that. what also works great is Pearl Izumi softshell PRO lobsters but size up one and then get wool gloves (I like the DeFeet ones) to wear inside them. solid down to 20 degrees-ish. and plenty of room for a chemical warmer, if you need it.
to be honest though, below freezing I really start to analyze whether/not it's worth it. I have to look at what the weather's been doing the last few days, how clear roads are, what the chance of black ice is, how much salt I really feel like cleaning off my bike, etc. then there's the extra half hour to get all the gear together and onto my body... usually means I focus more on just making sure I can ride on the weekends when I can go out for a bit longer, so it's worth all the hassle.
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