so excited to see a thread on this bag...i just bought one in perfect condition practically pre-owned (after authentification here of course)!
i bought it in black epi, not sure what color yours is? i think mine is pretty classic b/c it is black epi...i think almost anything in black epi is not hard to pull off.
that being said i could see why ppl might think it is a bit dated...at the same itme i think it may have been dated long enough that it is back in, just like neon or wearing black and white, which were both strong trends in the early nineties and saw a re-surgence a year or so ago.
to me, like the noe it looks good with today's leggings and skinny jeans...something about the big bell like shape works well with the up and down, tapered shape of slim fitting pants. it just really depends on how you wear it. i think also being young helps...in this case i am of no help then as i am in my early thirties, haha...but if you are a very young fashionable girl like my younger sister then it is not difficult to make old things look new.
at the same time, OP, i am sure if you like your bag you will look great with it no matter your age/style.
the only thing is for a shoulder tote it is too structured to be comfortable...that is why as much as i love it i am considering selling it. i will probably keep it as i bought it for a low price and owuldn't make more than a couple hundred from it...so functionally i don't think it's perfect b/c structured bags should be handheld in my opinion. and i agree it doesn't hold as much as you would think from looking at it b/c it is so structured.