Totally depends on your attitude, I saw a girl dressed in black with combat boots wearing a Black Reissue 227 and I thought it looked great! I think she had rhw rather than gold, but point being - it's how you wear it
they look similar to me and i would keep the reissue, smaller quilt and the leather looks much yummier imo
and the one on the left doesn't look like it's as well made as the reissue and it looks a bit cheap to me
and i think you definitely can wear a reissue down, that's the thing about chanel, i myself prefer to see someone wearing their classic or reissue with boots and jeans than with a formal dress
I actually just bought the exact same bag (on the left)! My SA told me it was called the "Cosmo". I do agree with everyone else that the reissue is more beautiful in a classic way, and I don't own a reissue myself so I can't really compare. But that being said, I love the other bag more and more as I use it! It is so lightweight (no extra flap, no leather lining), it's roomy, and feels very casual. And I love the look of the aged gold hardware, and how it looks like a skinnier version of the boy bag strap. And the leather is so buttery soft! Anyway, I hope you don't have to give up either of them, they're both beautiful!