hi hollie,
welcome to the dior subforum!
there's been a similar thread like yours which was posted by another PFer, perhaps you might want to take a read of it to see what some PFers think about the gaucho being a classic or trendy bag.
the thread is right over here:
http://forum.purseblog.com/dior/large-gaucho-saddle-bag-82555.html?highlight=gaucho
from my personal experience, i fell in love with the gaucho when the ad campaigns first started and it was just love at first sight. i had to wait a good long while (nearly a year i think!) before i finally could own one, but it was well worth it and my love affair with the gaucho never once died during that long wait. I guess it's a matter of how much you love it because even if it weren't deemed as an "it" bag a few years from now, as long as you really do like it a whole lot, it wouldn't really matter.
that said, i do think it's a classic in its down right. it may not compare to the lady dior (which if you're looking for a classic staple piece, i'd absolutely recommend!) but i think the gaucho gets better with age actually (since it's supposed to look distressed/aged). plus i can see the gaucho being worn dressed up or down with just that nice touch of edginess to it.
i can't recommend the gaucho enough, and also you might like to take a look at the other threads (and dior.com) since there are just more and more variations of the gaucho coming out (in particular, the cruise collection gauchos - check out chrystalline's gorgeous white one:
http://forum.purseblog.com/dior/my-white-metallic-strap-gaucho-70710.html and also the new spring ones from dior.com)
i hope it helps a little, and i'm sure other members will chime in with their opinions soon.