Which is a better investment? Chanel or Rolex?

Rolex?
Sorry, but not classy.
Blancpain, Vacheron Constantin are a great choice.
And about investment, forget it
You should better take care of your belongings, let them look like new ones in case if you want to get rid of them.
 
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I don’t think bags or watches are financial investment pieces but then it also depends what do you really mean by investment piece.

If it’s emotional investment Rolex for sure as I inherited my grandpa’s Rolex and means the world to me. Every time I wear it I feel like my grandpa is with me and helping me in my decisions. I hope to leave something like this (jewelry or watch) for my kids which will remind them of me when I’m not around.

If by investment you mean cost per wear then again Rolex makes more sense as you can wear them everyday for years whereas bags may need rotation to keep them in good condition.

So IMHO Rolex is a better option than bag. In any case good luck with your decision.