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I have a bag with grommets but I thought too much hardware for a 51 yr old!
Jessh - do you prefer black bags with black leather jackets? I have olive Hammitt but again, not loving grommets. I have a mini blue bucket Mansur Gavriel but the blue is bright and I think takes focus off jacket. My Vuitton bags , I'm not loving with my black leather either. Unless I use my emp speedy 25 in the purplish brownish color. I forget the name of it.
Jesssh - I totally love your ideas! Do you work in fashion industry or retail? I have a Damier azur bag but afraid it might get black color transfer on it from jacket. I don't know if that happens with leather. Definitely with denim.