As a general rule dressing in layers in cold climates is better than donning one, heavy garment. Particularly if you will be active and working up a sweat you want to be able to take off a layer or two while you work and then re-don them as you “cool down” so you don’t put yourself into a hypothermia via wet clothes.
If you’re going to be essentially static then layering is not so crucial.
Overalls and a outer jacket to start work might be a good way to begin as they can go off and on reasonably easily.
You also have to consider “how cold is it?” Work above freezing is different than work below freezing but above 20 degrees F. and that’s different that deep cold below 20. Layering is still the Name of the Game.
Here in East TN we don’t worry too much about deep cold. But having lived 16 years in IL, 7 in WI, and 4 in MI has given me some experience!!! 
Personally, I start with a good set of “long johns.” I like the silk offering from Cabelas. They are modestly priced and wear reasonably well. Over that goes a pair of appropriate trousers/breeches along with a good shirt. Above freezing I often wear cotton but sometimes wool. Below freezing it’s wool. Over that a wind/rain resistant layer. In deep cold I might add a wool sweater or the shirt. Don’t “bind” yourself up as you want some air circulation to prevent sweat accumulation. Don’t neglect your feet and head. You lose about 75% of your body head through the head. Meaning a warm head means warm feet! Whodda thunk it?!?!?!
Mounted I wear a helmet and my wife made some fleece inserts to cover my ears. Afoot it might be brimmed hat (likely in rain) or wool “watch cap” (left over from my midshipman days). Always ear covers. Wearing riding boots it’s a silk sock liner, a lightweight wool sock, and a Gortex oversock. I have a pair of riding boots that are a bit oversize and these fit. Don’t put too much in your boot as that will restrict blood flow and that’s bad if you want warm feet. Afoot I delete the Gortex if the boot is waterproof (like a Muck Boot). Again, don’t overstuff the boot.
I also have my “lucky green scarf” and my white, mondo kool Aviator scarf (one silk, one wool). Keeping your neck warm is important, too!!! 
Cabelas also sells silk glove liners. They take whatever riding or work glove you might be wearing down about another 15 degrees.
If you don’t like silk there are some synthetics available. I don’t like them but that might be just me. They are, I’m told, reasonable alternatives.
In the winter “dress for success” means dress such that you can do your job without getting sweated up and risking hypothermia. There are many variations on this theme. Find the one that works for you.
Good luck in your new home!
G.
