We are the same age, and I went through the same things a couple of years ago.I am refining my Chanel collection and would appreciate some views. Here are bags I currently have + an additional vintage beige clair medium classic flap not pictured.
So I have 2 medium classic flaps in caviar - black with shw and beige clair with 24k ghw; 2 large (226) reissues - in navy with ghw and grey shw (50th anniversary edition); 1 old medium Chanel Boy in pink Lambskin with vintage ghw; 1 grey camera bag in calfskin with ghw; 1 beige Clair caviar WOC with ghw and 1 red square vanity in lambskin with champagne ghw.
I am thinking of selling both the grey 2.55 and grey camera bag, and replacing it with the grey mini rectangle. BUT my grey 2.55 is a 50th anniversary edition so I am thinking twice about selling it even though I seldom reach for it.
Also thinking of selling the pink Chanel boy bag. Mostly because the style is edgy (I’m past that stage), chains are heavy, and I find that I reach for pink bags less as I head into my 40s. Boy bags don’t seem to be the rage anymore, do you think?
I am also thinking of selling the beige Clair WOC and replacing it with the dark beige / caramel mini square or rectangle. I find the WOC size too small for me, and I worry about color transfer when carrying it cross body. But a WOC is classic and their prices keep increasing..I am afraid I will regret if I sell it. Also, I’m thinking I may reach for it more when my kids are older and I don’t have to carry so much stuff around.
Are there any other bags you would sell or add to this collection if you were me? I am trying to curate a timeless and versatile collection that I can pass on to my daughter (so she doesn’t have to fork out $1xxxx for a Chanel bag when she grows up)!
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I will definitely sell the boy first, more than the look is the size for me.
I will sell the gray camera bag next ad you will replace it with another gray handbag.
The 2.55 gray you seldom reach for it, I think that should be your main reason to let it go, but… this is a classic and if I were you, I would not sell it until I am already curating my collection and see if things are working out better for me.
As per the WOC, if you want to sell it because it’s too small then I would agree with you, but if you are replacing because you are concern about color transfer, then I am not sure a dark beige/ or caramel handbag will be any different. Any colored handbag unless black could suffer color transfer

I am bias about vanity as I am not a fan, maybe selling it and replacing it with a black WOC?