I suppose it really depends. I tend to pick up lenses that have something I like in the image. I have several lenses that have no character, but I use those for work:
Nikkor 28-70/2,8 AFS
Zeiss Makro Planar 100/2 Ai
P.C. Mikro Nikkor 85/2,8 ED Ai
Leica Elmarit 28/2,8 ASPH (no character to speak of)
But I love the 85/1,8 K for its swirly bokeh and pleasantly soft but sharp centre.
The only time I worry about perfection is when I get paid for a very specific look, but otherwise, when shooting people, etc., I prefer (as do some other photographers) softness, 'character' and a lot of natural vignetting.
I have no idea what 'hipster' is as I don't live in America but I was told what a hipster was and it seems that it is anyone who has a chip on their shoulder about something and cries about it. I think that sounds like everyone. Petzval lenses take the 85/1,8K to the next level. Anyway, I'm in my thirties: I'm not worried if someone calls me a hipster.