I have this idea to walk to the train station in the morning. That would be a 2.5 mile walk each way. That is the distance it would be nice to bike. 2 miles is about the maximum I want to walk given the time commitment too.
You need a parka. Two condition:
1) You live somewhere actually cold (days where the high is below 0F)
2) You actually spend time outdoors (walking from your heated house to your heated car does not count; waiting for the bus 30 minutes to an hour at a time does count).
A big, heavy, fuck-you cold kind of jacket.
Alternatively, you do not need one, but you wear a couple of sweatshirts. This approach, actually, does work, given that you layer appropriately.
But this post is gear I want, not gear that works. And I want a parka. -> I have one.
Overalls. I have some from my skiing days and I could never understand why people did not opt for those instead of pants. Bibs stayed up always, had range of motion, and snow never got under your jacket and into your back and butt; pants always did the opposite. Pants were falling down and leaving people cold. I guess bibs did not look as cool, and came in every color as long as it was black. Bibs would finally let me have something warm to wear in the winter on my legs. Additionally the pair I want have a work-wear cool vibe which would allow me to wear them in casual, outdoor activites...-> I want a pair of Patagonia Iron Hemp Overalls. Probably in my size. Probably sized up one belt size.
A pair of boots is good for daily walking around, above ankle height should do it. A pair of high boots is gooder for shoveling snow, walking out to the barbage, etc.
Basically, what I am learning is that there are fashionable warm clothes. It is really nice to be able to slip something on quickly and go outside.
A bunch of sweatshirts is good, but you can easily put on or take-off a parka and now, well, it is like super warm.
Same with bibs, easy to take on and off.
The use cases are waiting for the bus (cold below 10F, or colder below 0F), mild 20-34F, or quick trips outside < 15 minutes.
The image I have in my mind is walking around a frozen lake at night. I want to be warm standing around there. But how often do you actually do that?
You could wear a gorilla suit.
What about going to a brewery and walking around? Wearing the bibs is nice because, you can be warm, and it is just work wear.
What about going somewhere nice for dinner?
You are going to be dressing more chic for sure. And probably traveling in a car or lyft.