Winter in deep snow,: Sorel Sentry boots that I've had at least 25 years. They don't make the steel toe Security any more, but the closest current are the
1964 T Wool boot; 10" boots with the felt liner.
Every day of the year when not in the Sorels:
Salomon X Ultra LTR GTX GoretTex, breathable, lightweight, cushioning, just wonderful!
40 years ago I wore 5 pound backpacking boots, then 25 years ago I found Vasque Sundowner GTX soft leather, Gore-Tex, lightweight. But I left them muddy and outside, and they were ruined. New ones were hard leather, heavier, and cheaply made. I'd kill for some old-style Sundowners.
Then I went to Merrill Chameleon Gore-Tex boots. Lightweight, comfy, cooler than the Vasque, but not as much support, and the sole wore quickly and got slippery on wet riocks. Two years ago, the guy at REI Seattle convinced me to try on the Salomon after I was going to get Merrill Moab's (the successor to the Chameleon.) Half a dozen steps later, I was sold. The most comfortable hiking boots I've ever worn in 40+ years of seriously caring about my boots.