Hypno
Crow
Furthermore, what are the odds you'll like wearing your pair of $500 shoes for 30+ years anyway? Most peoples fashion sense changes a lot over time.
I have a pair of Johnson & Murphy cap toes that I bought in 1994 that I still wear and have been resoled many times. I think I paid $139 for them at the Genesco outlet in Nashville.
I still have a solid navy 42L Hart Schaffner & Marx suit that I bought in 1994 for $550, but it hasn't fit me for at least 20 years. Will give it to my son. I have considered giving him my Tag Heuer watch that I bought in 1999 (which I bought for myself when I reached some personal goals) but its not really in style any more. It looks fine, like the picture below but with a black face.
Both the shoes and the suit are classically styled and still in fashion. Even the watch is still a solid fashion choice. I do agree with you that it is foolish to pay big money for something that will go out of style.