Lets start with our feet and work our way up.
Move over boot socks, you are absolutely useless to my toes below 30 degrees. Despite my feet getting absolutely clammy and gross just thinking about these bad boys at any other time of the year, I live in them come winter. Fuzzy socks are great.
Ok I know what you're thinking. That's a picture of Uggs. But bear with me for a second. I got a pair of Uggs in high school, which is now like 8 years ago (WTF?!?!) and as a result they're pretty beat up. This makes them the perfect barn footwear, because I don't feel badly about them looking any worse. And here's a little secret equestrian boot manufacturers... sheepskin is 1,000 times warmer than anything you're lining my boots with.
I'm not sure about the rest of you, but once my hands get cold I am absolutely MISERABLE. It's almost impossible to do anything around the barn with numb fingers, and these gloves usually do the trick. They are fleece, so not exactly waterproof, but I usually don't have an issue with them, and I just think fleece does a better job of keeping things warm.
Ok all you Southerners, go ahead and tune out because you will probably never have to touch these bad boys. These are Schmidt coveralls or bibs, and are basically the knockoff Carhartt brand. Because I am poor. These puppies are responsible for making me look like I've gained 100 pounds, make me 1,000x less mobile, but are absolutely essential for keeping me from crying after an 8 hour barn day. I usually wear a pair of breeches underneath, incase I need to strip down and get on a naughty school pony, but between the two layers I am warm all day.
As far as warmth goes, layering is your friend. I typically begin with a plain, fitted long sleeve t-shirt. I like it to be fitted because it keeps the heat in better, and if it's too loose it can ride up, and it is IMPOSSIBLE to access your first layer once all of these layers are on. On top of that usually goes a thin, half zip fleece. I have a couple different ones and really don't have a preference for any brand in particular. They all do the job. On top of everything goes my sherpa lined Schmidt jacket. This is hands down the warmest jacket I own and don't know what I ever did without it.
To top everything off is a headband. I actually just crocheted one myself, mainly because I hate feeling like my ears are going to freeze, crack, and fall off.
The best part about all of this, is that I literally wear every one of these things shown above at the same time every Saturday. I look absolutely ridiculous, and I'm sure my lesson kids think I'm weird, but there's no way I could make it through the day without all of these things. Now to prepare for the snow tomorrow!!