I'm a big fan of the idea to 'buy it for life'. Most people focus on durability as the key criteria for buy it for life. And, yes, the stuff needs to be durable... but the far harder, less common aspect is that you need to still love it in a decade, let alone a year.
How much stuff do you love today that you loved 15 years ago? 10 years ago?
For me, the list is short.
With that in mind, a key question needs to be: is it timeless? Can it survive changes in taste or in lifestyle?
When you find the rare gems where there is a clear yes, you know its a win.
(PS - All tattoos need to meet this criteria!)