If you're looking for scotch, The Last Hurrah at the Omni Parker House is a great option. One of the best scotch bars in the country.

I too subscribe to the "Cheetos method" of temperature regulation. Sounds like you've got a solid plan. Boots aren't hugely necessary unless there's snow on the ground, which there shouldn't be. Good socks should be fine.

Layer, and keep your extremities covered - ears and fingers. If I have to be out in this for any amount of time (like while waiting on a bus) I'll do tank top > long sleeve thermal > long sleeve top shirt > fleece or windproof jacket. It's less about having a "heavy" coat as it is about keeping your core warm. Definitely have gloves and a hat. Have fun!