Okay so this might seem like a silly question, but I am from South Florida and have never experienced an actual winter. The coldest it has ever gotten here is probably like 40 degrees. Anyway, because of this, I really don’t have much of an idea as to what kind of winter apparel I will need to purchase for when I get to school in August. I’d really appreciate a list of recommendations for what I should buy.
Snow boots, long underwear, a good winter coat (The North Face, Columbia, something from REI that will last forever), beanie (I like SmartWool), good socks (Also, SmartWool), gloves. As time goes on you will likely accumulate several of each of these items, as well as other pieces that you probably don’t wear in South Florida, like cute sweaters, ankle booties, riding boots, etc.
I moved from Seattle (where it stays between 40* and 80* year round) to Denver (between sub zero and 90+ degrees - sometimes seemingly in the same week!) a couple years ago. The necessity of a pair of snow boots cannot be emphasized enough. Get some high quality ones (The North Face and Sorel make some VERY cute boots) and you will never want to take them off in the winter.
Congrats on Georgetown!
@Cloudy206 Thank you so much! You were really helpful 
We are in the same position. I did purchase a nice Eddie Bauer winter parka so far. Kid doesn’t think he needs boots, but then again, he thinks 40 degrees is freezing. Just wait until he gets a taste of Boston weather.