Walking in the cold - clothes, gear, tips, etc.

I walk year-round, and I always find the cold a big adjustment. First, if it's below 40, I almost always wear a knit hat or ear coverings. I also wear gloves, and if below freezing, 2 pairs. My legs get cold, so I wear heavy sweats, or if leggings, sweats over them. I also bought a full-length down coat, and if I wear that, my butt and legs are pretty much covered. I can't walk as fast with it, but I'm warm. I usually do a mile and a half to two miles a day, but when I first start, sometimes I can only stand about 3/4 to 1 mile. However, with each day, my body gets acclimated, and I can walk longer. Our bodies get used to cold, just like they get used to heat, and by February, 35 degrees feels almost warm. I don't typically bring water when walking unless it's really hot; I just hydrate before and after.

I wear about 4 layers when it gets below about 50 degrees (down to about 10 I am ok) - a tight sweat wicking shirt/bottoms, a tight warmer long underwear type, a sweatshirt/pants or thicker shirt, then a jacket. I wear two pairs of socks - one fuzzy, the other wool - along with hiking type waterproof shoes/boots (cause wet feet suck). I also carry a mostly empty backpack with me - then I shed layers as I warm up, or in case I over did it. I keep extra gloves/scarf in the backback in case I underdid it. I also bought rechargable hand warmers I keep in my pockets so sometimes I dont bother with gloves.
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- Dont bother too much with brands - hit up the thrift stores and go for quantity. For under $25 you can get everything you need, and usually brands you couldnt afford new anyway. Look for stuff you can layer, then the quality doesnt matter too much anyway.
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- Put on headphones, and ignore the other people and their clothes. I promise, they are ignoring you and yours.

For 3-5 miles in weather above freezing, I don't think you need to overthink this. Just experiment. Put on some medium weight socks, a comfortable pair of pants, a long-sleeved base, and a jacket or hoodie. Take a light hat and light gloves. If you feel hot, take off the hat and gloves, and if necessary, unzip the jacket. If you feel cold after 5-10 minutes dressed like that, loop back home and add another layer. Leggings under the pants are good for the legs, while another jacket (or a jacket over the hoodie) is good for your upper body. If you're too hot with a hat, but your ears get cold without one, then buy a headband that covers the ears.

If you're alternating jogging with walking, your main concern will probably be that you're getting too warm. Having a top layer that you can unzip helps immensely. In my run yesterday (around 40 F), I started with a lightweight long-sleeved top and a lightweight jacket, zipped up. I finished with the jacket unzipped and flapping in the wind.

Fancy technical gear is all well and good if you can afford it, and the colder it gets, the nicer it is. But cheaper clothing works well. Just remember that cotton isn't ideal because it absorbs water and gets clammy, and that layers allow you to easily adjust temperature. I will wear cotton jeans when walking or hiking in the cold, but usually with a synthetic or wool layer below them.

If you get into running, that's the point where technical gear that is warm, breathable, and wind-resistant becomes important, especially below freezing.

No one is really going to care what you wear when you're walking.

Costco has nice running tights/leggings and thermal long sleeved shirts for under $20 each.... gloves, cheap toque and a light jacket/sweater that you can take off when you run and get hot.
Regular running shoes. Drink water when you feel thirsty, carry a scarf, but you might not use it..
Dont overthink it, it's not an expedition to Mount Everest, its just a short walk/run....
Have fun!

I wish it was that warm here I'm in Winnipeg where winter is not tolerable, -Im currently wearing northface goosedown jacket when I leave the house, ski mask if I'm walking somewhere.

I walk everywhere, summer or winter. And by winter I mean Canadian winter (not Winnipeg winter though, that just defies logic). I wear layers, a t-shirt, then a sweatshirt then my down winter jacket, unless it's above freezing then I wear a sporty anorak. I usually just wear leggings and one pair of socks. If it's windy, I wear a pair of nylon track pants over them. Usually a knitted head band, a pair of gloves, and a knitted scarf if it's really cold.

And every single time I am sweating. I find myself unzipping my jacket almost every time. I don't care about that though, I'm not overheating, so I just make sure that the layers I'm wearing close to my skin are appropriate for sweating. So usually old t-shirts or dri-fit clothes.

As for shoes, you summer ones will work well unless it snows a lot or gets icy where you live, then you'll want ones with a better grip.