Great thread idea!
My sister bought me this Nike jacket for my birthday 2 months ago:
https://www.nike.com/t/therma-mens-training-jacket-7DRA7m/864103-382
I don't think I've gone a day without it (don't even need to wash it, if you let it air out it smells like new). Probably wouldn't do well in freezing cold, but its perfect in chilly weather.
Incase City backpack purchased in 2014:
https://www.incase.com/products/bags/backpacks/city-backpack
Been through hell and back, only thing that's worn is the gray has gotten a sunblasted and turned a little blue. Layout and compartments are smartly integrated, looks sleek, extremely comfortable and great airflow. I'm a customer for life.
Timerbland Britton Hill duckboots:
https://www.zappos.com/p/timberland-britton-hill-rubber-toe-boot-medium-brown-full-grain/product/8906897/color/597504?ef_id=Wh4lFgAAAHT5YBpF:20180125055005:s
Bought them brand new, hit them with a leather sealer and then spent 2 weeks walking all over wet, cold, dirty Paris and then another week in muddy Normandie. They were pretty tired looking when I got back to the states, but I hit them with some hide food and they look good as new with some slight patina.
And to be cliche: All the Apple products I've owned have far exceeded expectation. I'm still using the same Macbook Pro I bought in early 2011 that's working great with the new OS.