I use Lake MXZ302 (current version is 304), selected on the basis that dubbin will keep leather waterproof, but there's nothing that can be done about a leaky goretex liner.
Whatever you get, a size or two larger than normal will allow the blood to circulate and keep the foot warm, provided you can resist the temptation to stuff the space with extra socks.
Loose is warm also applies to gloves.
For water ingress via the ankle, a high ankle is best, with your longs on the outside of the boot (no stirrups). You can also improve matters using drysuit ankle seals, or the wrist sections off a pair of marigolds as a handier alternative.
Having said that, global warming has arrived, and last winter never warranted their use. I was wearing SPD sandals all winter, and only needed socks on 3 or 4 rides.
I used to use overshoes (MTB velcro), but they mostly needed replacing every year, weren't as warm as boots, and let water in more.