Stitchy, among people who really dress well, here is what their trajectory was (if they had good guidance at the beginning). I started a thread about this once but I can't remember the title. Might have been "simplicity."
Anyway, when you start getting serious about "building" your wardrobe and dropping serious coin, you have to get the basics. My first bespoke commission was a navy blue suit and a pacel of solid blue and white shirts. Then a solid gray suit. Then a blazer. Etc. I had to do this because I needed stuff that I could wear in any situation, over and over. I was going by what I had studied in Flusser and AA. But a lot of guys who are into clothes make the mistake of buying individual pieces that grab their fancy and that might be very nice but that are hard to pair. Then they have to go to a job interview and they have this lovely tom ford windowpane in the closet but no solid gray SB. And they are fcuk'd.
So, the right way is to start out with only the basics. Blue & gray for suits, blue & white for shirts, a blazer and maybe a couple of tweed jackets--brown or B&W herringbone, brown or olive gun club, etc--gray flannel pants and khakis, some solid ties, some repps, and some businessy prints or wovens. Voila. Most everything goes with everything else. Not literally. You still can't wear your white FC shirt with tweed and not look like a fool. So you need to know the basic rules. But if you have those things and rudimentary knowledge, then you can make a small total number of pieces go a very long way, without getting bored yourself and without boring the people who have to look at you.
Then once that's accomplished, the good dresser starts to get antsy. He wants to branch out. More patterns! More colors! More textures! More more more! He starts to look like a dandy. Nothing is incorrect, but the only time he looks sedate any more is when he has to.
Then eventually that fire burns out and he goes back to blue and gray, and brown tweed and gray flannel and repps and solids, etc., and lives happily ever after.