Most of my winter clothes are higher-end stuff from REI or similar mountaineering/outdoors stores – but I bought them all from REI Outlet during the 50% off sales where you get the odds-and-ends from the previous season for less. That Ground jacket, for example, still cost me $90 and is normally a $180 coat. I had never had such an expensive piece of clothing before, but damn, now I can see why the higher-quality gear costs more. It’s worth it, because the higher comfort level encourages you to get outside more, and high quality clothing lasts much longer. The coat is over 5 years old, the Grandoe gloves are 10, and the other things are somewhere in between.. and they get used every day during the chilly season.
The nice thing about this clothing setup is that it is still worn right over your street clothes. Even in the worst weather during my working days, I would bike to work in the full outfit, then could strip the outer layers off within two minutes and would be dressed as a regular office worker.
I can't wait for this wave to die down so I can go back to the office! Maybe even by bike.