With my watches, I always have gone for more classic styles than trendy.
I am extremely picky about my fonts, colors, hands and so on. I've tried to buy pieces that have a timeless quality about them.
OTOH Some of my colleagues believe that their watches are like tattoos - they represent a certain moment or event and want them to "mark the time of purchase".
It's not a debate about defining either. It's about your own tastes and whether you mind if your piece looks dated in a few years.
For me, the only exception had been size. I've got some 36-38mm pieces that I simply never wear because they are just too scrawny anymore.