This is not going to be about where you should buy/how you should buy clothes, or what you should buy. There’s just something special about having some items that have lasted you forever, and that you still have managed to wear regularly through personal style evolutions, wear and tear, and couldn’t dream of ever getting rid of. It’s part of your uniform and yours alone even if there are millions just like it elsewhere in stores, in closets or thrift/resale stores. They don’t even need to be expensive or luxury items.
Personal favs for me include a plain light blue oxford button down from J Crew 10+ years ago, a Barbour motorcycle jacket of a similar age I bought after one of my first post college jobs and moving to a new city, and then also an Ohio State football (alma mater!) t shirt I got as a kid before even attending the school, which still somehow fits me believe it or not!
Would love to give items like these to my future kids!