Clothing for 50+ Windy weather

Look for what they use for the cold weather gear in the military. Maybe you’ll see something cheap at a military surplus. Shit works.

Every winter I wear the same jacket I've had since I was 16. Its a green military jacket I got from an Army Surplus store. I wish it was waterproof fully but it works great for windy days. Its seen some better days but still it has no holes and the zipper still works great.
 
Wear parachute pants or those lightweight hiker pants with base layers and a windbreaker. Add layers in between depending on how cold it is.
 
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Use layers; something like a windbreaker over a fleece over a wool sweater over a good shirt if it's really cold. Don't forget a wool cap, gloves, and of course long-johns under your pants. Also keep a couple off extra pair of wool socks. ALWAYS have extra socks... One step into a puddle at night or just the need to double-up will make you a believer. I spent an entire winter in Chicago, and the cold wind blasting over the ice is no fun. Layers are your friend! Stay warm.
 
I think it really depends on your tolerance for colder weather.

Housed at the moment but did a week long trip recently to visit traveling friends. Temps were 10°C max during the day and I wore two t-shirts, a tattered hoodie jacket, a fishing vest and ragged jeans (almost more holes then denim) and I was fine. I even walked around without shoes a few times.

Granted, it was a bit cold at night, but then I was mostly in my cozy sleeping bag. :)
 
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