Many people refer to cotton as cotton = killer, in the winter. You sweat or get cotton wet and have it against your skin and thats how you get hypothermia and/or frostbite. You definitely want Under Armour or Silk underwear leggings and top as your base layer. Same goes for socks, so some sort of base layer sock, I again use Under Armour, then definitely a wool sock as your 2nd pair on top. When your walking through the woods, rowing your boat, etc. You will sweat, but you dont want the moisture against your skin all day. UA base layers wick it away from your skin.
Like anything else, you get what you pay for. Im biased to UA because for $100 total ($50 for leggings + $50 for top) I have zero complaints in temps down to 0 degrees. I honestly hate the cold, but with decent boots and outer layers, as long as I have UA Base 2.0 as my base layer I can sit 8-10 hours in temps below freezing without any issues.
Depending on the temps/winds/etc....I wear a full mask or just a dickey. I always wear a tight beanie with a heavier one over it.
Last but not least, hand warmers. They are so cheap and last for 8+ hours, I keep them inside my gloves against my bare skin. Anytime my fingers get cold, I just make a fist and feel the heat.