Just a quick update - I'm looking out the window at snow. It will probably be melted by Thursday, but I'm wearing the shearling today so it's nippy. Definitely NOT flip flop weather!
Also, something to remember here, it's not like other areas where you can go from a warm building, to a warm car, to a warm building. There's always a walk involved and even subway platforms can be super cold in the winter. Don't think you'll be okay with a hoodie in 40 degree weather.
From weather.com the local 5 day forecast is:
Tues. - High 34
Weds. - High 38
Thurs. - High 41
Fri. - High 44
Sat. - High 51 (that will be a nice day!)