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Overshoes are great when it's pisswet/cold. I can keep going a lot longer in shit weather if my feet are warm and dry.
The kit you'll need will depend on how warm you tend to run. I spend most of summer sweating and most of winter at a reasonable temperature.
One thing I wish I'd bought earlier was a Lusso Repel Corsa jersey and repel armwarmers. Bit pricey new, but picked them up cheaper from ebay. Windproof and waterproof/resistant but not boil in the bag. That jersey with a short sleeve base layer and the armwarmers sorted me out even in sleet/snow last winter.
Oh, and a buff/neckwarmer makes a huge difference. Great for the first chilly mile or two, then easy to whip off and shove in a pocket once you warm up.
Good warm gloves are also a must.
For the really super-cold days, I ended up getting a Lusso Aero+ winter jacket. Not stylish like Rapha, and RRP is pretty pricey but it's amazing. Completely stops all windchill, not plastic, not boil in the bag. Was only useful for me for 0°c and lower, but a proper lifesaver on those freezing cold days.
You may have gathered that I like Lusso kit.
It's not particularly stylish (in fact, some of their stuff looks awful) but their kit is made in Manchester, very functional and great quality and their repair service has been awesome when I've had to use it.
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TurtleRecall
This winter will be my first commuting sole by bike (no wimping out in a car/bus).
What essential clothing do I need to get? What can I scrimp on/have to spend cash on?