"Shoes in general" depends more on socks, then. Start to learn about socks. If nothing else, they're cheaper than shoes. Worthy of note: I live nowhere near Siberia so my conception of "wet" and "chilly" may pale compared to yours. It seems that you're not looking for workout headphones, which means the world is your oyster. However, the good ones will still have a cord. Sorry.
So I spent six weeks on Mount Rainier, 12 hours a day, 6 days a week, in the wettest winter on record. And I was given a truly meager budget to get comfy. But far and away my best bang-for-buck purchases were: 1) super-cheap Cabela's socks 2) $160 head-to-toe Cabela's camo coveralls I was surrounded by people wearing $3k in Arcteryx and I had 'em beat. Everyone laughed at my camo until they discovered I was the only mutherfucker that was comfortable. That realtree shit? It's no joke. Cabela's sold me an insulated pair of pants, a fleece, a jacket and a removable hood that makes no noise, has no odor, and can literally be submerged without getting you wet. It is the shit. If I could find the exact same ensemble in something other than realtree I'd be in heaven. Tellin' ya. I'm a big booster of REI and actual, you know, exercise but the huntin'fishin'froadin' crowd has the sit-on-your-ass-and-not-freeze gear handled and they do it for pennies on the dollar what REI wants.
I'm a fan of good socks. If your feet feel cold and you're wearing cotton socks, try wool or synthetic socks. Cotton traps moisture against your skin and makes you feel cold while wool and most synthetic fabrics do not. Wool socks can be made lightweight; they aren't only for cold weather. Merino wool is a specific type of wool that's popular and not itchy. A lot of brands use it, and my experience is with Smart Wool and Darn Tough, two popular brands available in my part of the US.
A decent driver requires decent power. Wired headphones draw this from the jack, and the headphone amp driving them. Wireless headphones must draw that power from on-board batteries, which also must power the wireless link. It's a choice - do you want fidelity, light weight or battery life? Pick two.
Can't do that. I have no idea which even might be good, since I have no experience in the field. That being said, I have been thinking about it and figured that wired headphones can't be all that bad, considering how little real trouble I have with them. I'll be following the recommendations already given in the threads and see what I will come up with. Thanks for the help.
Its just a nice luxury. Great for running I can totally zone out on the track and just focus on running and music, they never fall out or get loose. I think Ive probably spent the same amount over the years on IEM's Ive destroyed due to shitty quality.