I save up, buy nice outerwear, I get what I pay for, it lasts me 4+ years. I have used the same jacket for the last five years. I just replaced my pants with some used patagonia ones for $60, they are still bomber. I plan on buying a new jacket for next year, probably spending in the $350-$450 range. I expect it to last me another 4-5 years. That is better then spending $250 on a jacket and having to get a new one in a year or two like many people on here do.
I also don't try and keep up with trends, they are usually short lived, and ugly to boot.