I got into the game late 2009. For about 2 years I bought a lot Epaulet, BoO, Rogue's Gallery, etc. None of that lasted, so my oldest clothing pieces now are probably around 3 years. It matters a lot to me how long things will last, one of my problems with Schneider shirts was that I felt like they were going to disintegrate in a month with my lifestyle. My oldest piece is probably W+H x Dayton boots I bought from Farinelli's (lol I loved that store so much back then) and an Our Legacy shirt I bought at Mr Porter's first sale that has faded about 10 shades lighter. Love that thing.
At this point, I don't think my tastes will change too dramatically so I always buy with the intent of keeping it for a long time. I feel like after 5 years of experimenting through many looks, the only aesthetic change I can see myself having is towards MC due to work stuff, but otherwise I think I'm set