timeless classic? or one off originals?

today I was doing my usual browsing around net-a-porter and such websites and wondered to myself.. every season we crave something new.. Its only human. (thats what the evil spirits tell me when my credit cards max out) and I thought to myself.. what would I rather have? Classic pieces that I may blow loads of cash on.. or those not so expensive 'in the moment' items that we know are hot for the season and may come back at some point during our lives? I mean.. can classic just get boring and serious? what about the one offs? cant they get too eccentric and wasteful? Does one bow down to each season when told to jump through hoops? who knows. More opinions necessary.