No Stupid Questions

Unless you have a husky or malamute, you need to protect their paws and ears. Their paws will be in contact with the ground, and their ears don't have any insulation at all. But that's not all. At -20 F exposed skin can develop frostbite in 10 minutes. So bathroom breaks should be short. Longer hikes should include boots, a jacket that covers their belly, and a snood that protects their ears. Dogs really shouldn't be out in that sort of extreme weather unless they've been bred for it.

https://www.rei.com/learn/expert-advice/how-to-dress-in-cold-weather.html

Good guide from REI, not an ad you don't have to buy from them specifically, thrift stores will probably have most things you don't have.

https://www.rei.com/learn/expert-advice/how-to-protect-your-dogs-paws-in-winter.html

And another guide for dogs.

For you:

Long johns (thermal underpants) or if you're caught unprepared then 2 layers of pants, undershirts, layers layers layers of shirts and sweaters.

Balaclava and/or hat and neckwarmer/scarf. Good gloves.

Not a dog owner so I can't give good advice, but I have seen many owners around give their littler dogs sweaters and boots.

Check a frostbite chart based on windspeed and temp:

If it's just a short pee out and back in, and it's the 30 min zone then should be fine without much if you had to, it will be uncomfortable but not too harmful. For full-on walks or anything in the 5 min zone you should prepare yourself and your dog well for it.

I grew up where it'd get that cold for awhile yearly in Canada, I can't say much about dogs but that's about where it starts to feel really cold without wind. Like another level was reached compared to say -20 or -25C (-20F = -30C). I also used to do a lot of outdoor stuff with a school, when we went out layers was a big thing (probably not as necessary for walks but it doesn't hurt, extra layers can trap heat to keep you warm). You'll want some will socks, insulated footwear, probably a scarf or some face covering at the very least. When it's windy it bites really hard and you don't feel like you'll get warm for ages. As for layers, well in that weather we'd wear polypropylene underwear, beneath everything may be overkill for non active work but you'll probably want some full underwear for anything longer than 30mins. Of course exposed skin is bad so gloves, mittens are better since your fingers stay together. If it's windy you'll want some sort of windbreaker outerwear. My experience is out of date so I'm unsure if the materials are correct.

As an example when we went out with the school we had day packs with us, carried extra wool socks and had multiple outer layers to swap with (fleece is very good but not good for final layer). There was also food and water in our packa but that's not really what you'd need.

So have a few outer layers with some wind protection, make sure to cover any skin for the most part (toques, scarves, mittens). For any dogs I'd think they should be above small side before going too far. We had a tiny dog growing up and his feet would be obviously too cold just from peeing outside in that to -40 weather.

Unsure if that helps or not, stay warm.

Edit thought I'd add, I've seen blisters on ears from -35-40C weather, but the person was playing hockey for an hour or so, but I've also walked home drunk from the bar at around -30C with wind, which wasn't awful but I did make a pit stop at a buddy's place after about a km, that was just jeans and parka type coat. I don't think I'd have tolerated as well sober heh. Also this info is close to 20 years old now so may be a bit fuzzy on some specifics, moved to a much warmer place thankfully.

I have a cutoff of around -20C for my dogo. Colder than that + winds is probably no go for most dogs not raised to be sled dogs.

On top of various other recommendations: down. Down / feathers are extremely well insulating. Also lightweight, which is nice. You do need to protect it from moisture, though.

And you don't want to wear cotton. Modern polyesters are the way to go.

Those temperatures aren't too cold to take your dogs out, unless you have something like a Chihuahua. But getting them used to wearing a warm jacket and booties is a good idea, especially for the short furred one.

We're not in that cold weather but we have small skinny dogs with basically next to no hair. We use various layers including Hurtta dog jackets that I finally/just found the last couple months after looking for years. Hurtta jackets are made in Finland geared towards their cold weather. Their Extreme Overall jacket had a hood/snood that I combine with a double layered fleece snood that you can adjust by folding back to make them shorter and then adjust longer as they get used to it. We now walk in the rain with their snood extended fully so their nose is just poking out and they're ok with that. Their ears were nice and toasty at the end of the walk with the snood fully covering their ears this evening.

I buy snoods from K9 Voyager, Cappi's Jammies, or Spoiled Bratz Wear. All have been reputable vendors.

I also have purchased heavy duty snaps and and a snap fastener, Hapden snap fastener tool (had good reviews so I purchased and have been happy with). That lets me attach extra pieces like snoods or other gear to customize for the weather.

Well for you sound set. You want to dress in layers, and you want to avoid sweating.

I have no idea what kind of dog you have. Honestly here in Chicagoland my dad's had a number of rescue dogs over the years, and the answer depends on the dog breed. The smaller and less furry a dog is, the less you should expose them to the cold. You may have to have them just go to the bathroom on those little absorbent mats inside if they don't want to go outside. And the dog will let you know that it doesn't want to go outside in the freezing ass cold.

But if you've got a larger dog, especially a very furry one or a breed that likes the cold (like a husky for example) you'll have any easier time.

But the most important thing is to pay attention to your dog when you're outside; it'll let you know when it's not happy about where it is.