Try the EMS store near you,  They are a really good place to start, and their store brand Long johns are really good for the money,  the bergdalene  material they make it out of is long lasting, non pilling and less likely to take on odors than many other brands.  
Raising your core temp means getting your bodies furnace running better,  more excercise, getting more easily burned food in you, and keeping your self more active even in the home will keep you warmer all day.
Heat loss happens most at the head and neck, the wrists and ankles are two other places with major blood flow near the skin surface to allow heat to escape.  Limit those heat loss areas and your body temp will rise.    The old campers adage of "if your feet are cold, put on a hat," really is true.   A good hat will raise your temp tolerance a lot.   Turtle necks and other high necked articles of clothing also help, a thin balaclava under a another warm hat really is a great way to do it. 
in the cold, try hard to keep dry.    if you have to walk a distance to catch a bus or to the parking lot, keep your jacket open and your hat high on your head,  when you stop walking, zip up and pull down the hat.  This allows the natural perspiration to evaporate while walking and then bundling up when you stop retains that extra heat your body made.  
Your body makes enough heat to keep itself warm in amazingly cold weather,   it was not unusual for me to skate in just shorts and a t shirt during conditioning skates in cold arenas as I was just burning calories.  Most of us too have gone out jogging on cold days when the first hundred yards were freezing cold then shortly after we are sweating heavily.  
For  boots, the warmest are the pac types with a shell and a liner to keep you warm, the Sorel, Lacrosse and Baffin are really good names, remember that getting -100 degree boots for a ride on the T are actually going to end up colder than the -10 boots as they will get your feet sweaty enough to soak the liner and your feet will end up cold.   -100  boots will make your feet sweat in above zero temps.
In boston, the need for extreme gear clothing is usually unnecessary.   you will have a few below zero F days, but not that many, plan on good quality jackets, hats and gloves combined with a good pair of boots and you will do fine.    If you are working outdoors, then a good choice is the  Carhart brand, their insulated bibs, overalls, and work coats will stand up to heavy use.