A few years ago when my salary was sky-rocketing and I received my American Express Platinum Card (which starts with a minimum of $100,000) - I went on a shopping spree. Mixed shirts, mixed Ralph Lauren ties, slacks, socks, shoes - just about for every possible occasion imagined - all in the vein that my appearance could never go stale. Needless to say, I over bought and learned the lesson. These days I look for basic and repetitive functions where I can better manage my selections.
This forum has helped me immensely, including the purchasing of upper-end men's style pictorial books to help round out a wardrobe which will very seldom go out of style.
Members who post they rotate their AE shoes typically own over six pair for the rotation. They may also own over six ties and slacks to round out the day wardrobe selected.
As long as I purchase quality (which my parents taught me at a very early age), the materials and craftsmanship can last generations.
Last year I gave my oldest son a cashmere sweater with leather trims on the sleeves - which I had outgrown. It would have been very painful for me to toss it along outside our family - because quality clothes become a part of your family. But it was less of concern when I knew my son would take care of it.
Temper your emotions, not so much for the pocketbook, but for the matured approach toward becoming a better steward of your resources.
All my best,