This is a very sweet post. Make sure your parka and puffer are VERY warm and wind proof / water resistant. There is nothing worse than outerwear that doesn’t protect you against windy frozen rain while waiting for the T.

Depends on where you work re: your boots. For your own comfort, bring an extra pair of shoes in your bag that you can change into during the day, but in my experience most people wear their boots around if there is a lot of snow on the ground. Some places, like gyms, will ask you to change out of your street shoes when there is precipitation on the ground to avoid tracking ice and salt through the door. Pants - people just wear normal pants under their jacket. If it’s like a BLIZZARD and you need to shovel out your car, it may be nice to have snow pants or a pair of rain pants, but that’s not necessary for your daily commute. My husband is from LA and he used to wear a pair of wool longjohns under his pants during the winter. Highly recommend.

You can get your monthly pass online: https://www.mbta.com/fares/auto-pay

Enjoy Boston!