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How cold is "very cold"? I'm in Canada and right now it's -35C outside my house, approaching -50 with wind chill. If I was out there right now my main prep would be "holy shit get to any sort of shelter, outdoors is lethal tonight." I believe the city leaves the various transit centers open for people to bunk down in overnight under conditions like this.
Failing that, my first priority would probably be a wool blanket. Wool blankets are great at insulation, they work even when wet, and they can be folded up fairly compactly and worn as a shawl or cloak if a little mobility is needed. Though under tonight's conditions I wouldn't be mobile, I would have found the most sheltered place I could immediately reach and rolled up in the blanket in hopes I would actually wake up in the morning.
Cheapest I'd expect to find a good wool blanket for would be something like these $30 ones, so that's 6 or 7 blankets on your budget. Not too bad I suppose. Maybe there are cheaper places you could get some in bulk?
If I had sufficient blanket that I'm expecting to survive, my next concern would be frostbite taking my fingers, toes, or ears. So good warm mittens (for survival purposes in these conditions I'd prefer mittens over gloves), thick wool socks, and a hat might be good. Boots would be expensive and hard to ensure the right size for if you're giving this stuff out to random strangers, hopefully their footwear is loose enough that the thick wool socks will fit. I've always liked trapper hats, the chin strap keeps the ears and cheeks protected and ensures I don't lose it to a strong gust of wind or other circumstances. The nose would be left unprotected, so perhaps a scarf would be good to add to that - a scarf is like a little mini blanket and might be versatile if they need to wrap it around some other part of themselves for emergency cold protection.
This is all just off the top of my head, mind you. I've dealt with Canadian winters all my life but I've fortunately never had to deal with them as a homeless person, so I could easily be missing something.
Perhaps you could call up a homeless shelter and ask whoever's running it for advice? I'm sure they'd have more direct experience.
Wow, that is insanely cold. I'm glad there is shelter for the people in your city.
Thanks for your message - really appreciate the links as well. It will be -13 feeling like -23 with the windchill over the next few days. Here it will often be wet and cold rather than soft snow and cold so there is definitely a hypothermia/frostbite concern. I'll call up the shelters in the morning and see what would be most helpful; i will pick up some wool blankets if they have no particular preference.
If rain and wet snow are a common concern where you are then perhaps you could throw in some dollar store tarpaulins to go with the blankets. They'd be a cheap addition that could help by keeping them and their possessions dry. Even though wool can still insulate when wet it's certainly not pleasant and it adds a lot of weight.
The links were meant as illustrative, BTW, not necessarily a recommendation to buy those specific things. I haven't gone digging around for the best deals (and that would likely depend on your location as well).