I have the Chanel WOC so I can only comment on it. I’ve had it since March and have basically been using it almost everyday. I love it mostly cuz I can wear it crossbody and with three kids being hands free is a must. I also love it cuz it goes with everything - casual, dressy...
also if I need a bigger bag I just often carry both the WOC and my bigger bag and I don’t find it looks funny.
I have to say I really love the lady dior too and am putting that on my wish list next. I went to see the non-mini one in store and it’s a bit heavy (esp the patent leather version). Nevertheless I think I’ll get it one day in a pinky nude. I feel the lady Dior is more dressy but still so dainty and beautiful.
With the things you need to fit, I don’t think either should be a problem. I can easily fit my iPhone, cards, cash, lipstick, receipts, and my LV 6 key holder in my WOC. Good luck deciding! [emoji5]