I think the reissue is a little more "edgy" than the classic 2.55. One of the posters here, Star3777, has one in grey and it looks very cool on her. I say if you like it, go for it. I would love to have both - one for evening events (the classic 2.55), and one that can also go with casual outfits (the reissue).
If you really like it, and have the money for it, then I say yes! Chanel is so classic that it would be a lovely investment. But, if you are eyeing other bags (and who here isn't?), I would admire from afar, and get something else.