I got into nice outerwear because I wanted a smaller collection of better jackets that I would wear often. I really hate the feeling of clutter when you have a house full of poorly made garbage you never use. I currently have 6 cloth jackets and 3 leather jackets, but some of these are crappy old ones that I plan to ditch as I move to higher quality stuff. At the moment I only have one autumn/spring jacket, a bedford cord trucker from viapiana that I wear pretty much every day during those seasons and one HH jacket from JL on it's way. For winter jackets I have my shearling jacket from JL, an Iron Heart N1, plus my old pop's M51 and two vintage wool jackets I never use and have trouble justifying keeping around. I once thought about just having one autumn and one winter weather jacket, but if you ever needed repairs or something on one you would be SOL.
That's exactly how it started for me - I ended up with around 50 jackets. I replaced 8 crappy ones.