Wool base layer, insulated mid layer, rain/windproof outer shell. They key here is too add/remove layers as needed, dictated by the weather and how active you’re being at the moment.

I work outside during all seasons.

In the winter…

Layers. Layers. Layers.

Top half:

• Undershirt(or not - depends on how cold).
• Thermal long sleeve.
• T-Shirt.
• Hoodie.
• Jacket(or not - depends on activity level)

Bottom half:

• Spandex type briefs.
• Thermal Long Johns.
• Thick work pants (carhart/dakota/etc)
• Decent wool/cotton blend socks.
• Snow pants(or not, slush pants or full bib - depends on snow and temps)

just put your hands between your buttocks. That’s nature’s pocket. -Futurama

This depends on how cold, and how physical the labor is. The more physical the labor is, the less you’re going to want to wear (in general), because movement and exercise is going to keep you warm.

But, here’s a basic guideline.

First, no cotton. Full stop. Cotton will absorb mater, and then loses it’s ability to keep you warm. Jeans are an absolute non-starter in really cold weather. Leather is okay, but absolutely must be oiled and sealed against water (I’ve been experimenting with a beeswax and neatsfoot oil combination that seems to penetrate pretty well when applied with heat, but that’s more work than most people want to do).

Second, layers. Generally speaking, you want a wicking layer right next to your skin, insulation layer(s), and a waterproof/windproof shell layer over everything. Polypropylene long underwear is the normal technical choice for a wicking layer, and you can get polypro sock liners and glove liners as well. Wool should be your go-to choice for insulation layers; it has the fairly unique property of keeping you warm even when it gets wet, particularly because it’s really hard to get wool ‘wet’ (because wool is hydrophobic). Gore-Tex is gold-standard shell material; it gives you some level of breathability (e.g., allows sweat to evaporate out) while preventing water from getting in and keeping the wind out. With a good shell, you should be able to open vents to cool yourself down if you get too warm (and definitely cool yourself down well before you start feeling sweaty!) Goose down is great at keeping you warm, but does lose it’s loft–and insulating properties–when it gets wet. Depending on what you’re doing, you may want abrasion-resistant panels on your shell layers, as Gore-Tex isn’t as durable as, e.g. 1000D nylon pack cloth.

For boots, the US military ‘Mickey Mouse’ boots are pretty great. They’re several layers of rubber sheet, with wool felt insulation. You want to get them sized up a little so that you can get a liner sock and full cushion wool hiking socks in. All leather ankle-height hiking boots (Sorrel used to be one of the top choices, I’m not so sure any more) with lots of oil/wax based sealants and gaiters is another good choice.

As far as hands go, the same basic principles apply; a lightweight liner, a heavier insulation, and a shell layer. Generally speaking, you want mittens rather than gloves. If you must have gloves, then shooting gloves or lobster claw gloves are better than gloves that separate all of the fingers.

You’ll also want a good scarf–again, wool–and a long hat or balaclava, covered by the hood of your shell layer. The downside to a balaclava over a hat is that if it’s cold enough, your breath will freeze in the balaclava, leaving you with icicles hanging on your face.

This is what I’ve worn when I’ve done multi-day camping trips in the mountains in -20F weather. I’ve made mistakes–like choosing boots with different insulation, which kept my feet wet for three days straight–and the mistakes were painful. Poor footwear choices when bicycling at -20F has meant that I’ve had frostbite in my feet–not severe, thankfully, but incredibly painful as they thawed out.

EDIT As a final note - avoid anything that’s really constricting. Your wicking layer should be against your skin, but not tight. Anything that restrict blood flow is going to be a risk to developing frostbite. Shoes that are comfortable without heavy socks are going to be too tight with them. Depending on what you’re doing, you may need to make compromises. For instance, if you’re doing roofing, you’re probably going to have to get cotton, because that’s what Carhartt is available in, and you probably don’t want to be wearing $500 Gore-Tex shell pants for that.

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If you’re active outside it’s surprisingly hard to be cold to be honest. Beyond that the most important thing is having a wind proof layer on the outside, and probably some decent gloves.

Carhart overalls (knock off brands might or might not be good). A good sweatshirt. Unzip or remove as needed - different parts of the day and different activities demand different levels of outwear. At the end of the day find all the clothes you shed and pack them back home for the next days.

For chilly days the cheap “jersey” gloves work great: buy a case. You need a new pair every day, but they are thin enough that they are easy to work in and cheap enough that you don’t care about a new pair daily. For cold days the yellow “chore gloves” work great, keep a dozen around so you can switch when they get wet. Most of the time I just let them air dry in my car.

Only really cold days have breakfast and start later in the day.

The only think I can’t help you with is when it is -1C and raining. If at all possible stay home.

I prefer natural fibers because I think they breathe better and keep me better regulated. And as someone that works outside year round in the Midwest, layers are what work. I have found that keeping my chest the warmest, it helps keep the rest of me warm as well.

Just don’t sweat, or if you do, be down to the lowest layer possible. And when you go in, get down to the lowest layer to air out the top layers and to help regulate your body heat.

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Everyone here is correct, lots of layers and wool. The only exception is cold windy days, it’s damn difficult to prepare for wind. On a -40 windy day there’s not a lot you can do. Hand warmers, or even better heated gloves can be amazing on those days for when you just can’t get your hands warm. My girlfriend uses a heated vest regularly and she loves it. I also almost always have a large thermos of hot soup or tea to sip on on break.

On stupid cold days I’ll sometimes where two wool baselayers. I find the layers rubbing generate heat and that can be lovely.

In my experience, you dress differently if your job requires a lot of moving vs a static job. Second one is way worse when it’s really cold

Layers

Nothing is skin tight

Any exposed skin is going to be a problem

I drive a forklift so how ever cold it is outside I get an additional 8mph of wind-chill

So today is really going to suck as there’s 15mph winds coming in, so in one direction I’m getting 23 mph worth of wind-chill and the other I’m getting 7

Edit: Also overlapping seams are pretty important as gaps can let air flow in when in motion

One thing that helped me more than I expected was an insulated face mask. They’re usually marketed to hunters. A good one sits comfortably below glasses or safety goggles, and it stands just off your face except for the edge.

Adding this allowed me to be more comfortable in colder temperatures and strong wind with less layers overall.

Under shirt, underwear, spandex thermal tops and bottoms(think under armor), wool or heated socks, insulated Thorogood boots, t-shirt, heated vest, work pants, work jacket, warm beanie, thinsulate leather or fleece gloves that I may have a hand warmer in.

With that I can work all day in Midwestern winter and compromise very little range of motion. Hand dexterity does take a tanking with the thinsulate gloves but they are warm enough to keep my fingers feeling things.

I often am outside for hours and then inside for hours; taking off the gloves, hat, jacket, and vest keeps me from overheating inside. The real game changer for me was the heated vest and the spandex thermals. I was working outside in the 30s and didn’t need a jacket with the vest on low.