Highwaymanman
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If you look at that question logically... you need at least 8 Grail Coats/Jackets. Ahem (Ahem Ah Say):
2 for Fall, one brown one black. Leather lightly lined with wool or alpaca. For me 50's HB and/or Indy.
2 for Winter, probably one shearling lined and one good woolie. I'd go B6 or D1, and a real peacoat or Duffle, mebbe Irvin.
2 for Spring, same line up as the fall, cept you might swap out Hercules, Windward of LHB.
2 for Summer, A2's, A1's with plain cotton drill. Here's where you bring in your "beater" you don't mind sweatin' through and hitting the ground in.
Welp that's my "theory" and ah'm stickin' to it!
Worf
I'm with you in principle Worf, but in practice I see several potential issues at least with regard to my lifestyle. The first naturally, is cost. On one hand I view my jackets as investments and I have noted that a coat purchased by my wife at around the same time as my first Aero has begun to look it's age while the leather... well, you know how that goes. but the money needed to make that 8 jacket investment? Well, I have other responsibilities. When I hit the lottery, I tell myself, it's gonna be a jacket frenzy.
The next is that I want to put time into breaking my jackets in good and proper. One of them is absolutely fantastic and doesn't need any work but I confess my Aero (old oil pull) is a beast. if I had another 6 like it I'm pretty sure I would need to set some longevity records to get them all looking the way I want them to. In a way I'd rather have only a few pieces that I wore hard rather than many I just couldn't get around to wearing.