They are both beautiful bags MrsSB, and its very difficult, to pick one, the chanel reissue is really beautiful and i love the beaten up look of aged calfskin,the flap is equally beautiful, both are iconic classics.
. i have both lambskin and caviar, and i would say i like lambskin better. Mine has scratches on, but it doesn't bother me,as I'm not very gentle with my bags,sometimes its nicer to have a worn look,IMO,
I'm having an hermes moment ,bought my second bag recently, a beautiful Berline in swift leather, and I absolutely love it,
but the Kelly is very hard to find in stores, unless you are an hermes customer,or go to paris where by luck you can find them in stock sometimes,
The thing I love about hermes bags,is that they come in many types of leather,and colours,so even a classic bag like Kelly can look very contemporary in Clemence leather in a size 35cm for instance, and you can get the thicker strap ,which is wider ,and can be worn casually on your shoulder . Box calf kelly gets nicer with age,and looks less formal,it really depends on how you wear it really.m
My dream is a Kelly 35 or 32 in Clemence leather, either in etoupe or blue sapphire.
So I would say if you can find a Kelly then go for it.
Wether its a Kelly or flap/reissue , they will never go out of style,they've been around since 1950s, (2.55 and kelly) the first chanel was a 2.55 in jersey, and its still going strong,