The answer depends somewhat on the chore you are doing.
I wear a flannel shirt with a wool vest with insulated trousers. My coat is a Filson Tin Cruiser or a Tin Packer...those take care of the wind and rain/snow. The hat is (depending on the temperature and if the wind is brisk) also normally a Filson brand...a double Mackinaw (looks like something Elmer Fudd would wear, but it definitely keeps one's head and ears dry and warm)...or, if less cold, another Filson branded insulated hat.
Can't beat Filson gear for outdoor work. Not cheap, but long lasting and tough.
Gloves...heavy insulated equipment operator's glove. I have no idea of the brand...my wife brought them from Wyoming 18 years ago.
Footware....last year I used Muck Boots with thick socks under them.
If I can keep my feet, knees, hands and ears warm and dry, I'm OK with extended outdoor time.
Mine's green wool rather then read/black checks. This is one seriously warm hat!
This one is when it's in the upper 20's or low 30's. It has fold down ear flaps
Tin Cruiser...all around work jacket that is very wind resistant. Not insulated, so you need to layer in colder weather.
The Packer. If you want to work outside for hours...or ride your horse for hours...this is the coat. It's not insulated, but you can add a wool liner or other layering.
By the way..this tin cloth (oil cloth) clothing is very stiff when new...it does take a while to break in. Being impregnated with a wax (for water/wind proofing), it does have a certain smell to it initially.