Thought I would add my 2 bits worth.
I started carrying a "Man Bag" like Bag #3 below after college when I no longer carried a Book Bag with all my stuff in it. I didn't like having all that stuff in my pockets, so I switched to carrying a bag.
The when I tried Women's Jeans, Leggings, Skirts and Dresses the pocket situation got worse and the convince of a bag where everything is kept was just too much to give up.
I wanted a smaller, lightweight minimum carry bag that worked with Leggings and Skirts, so I decided on this little bag, Cell Phone, Wallet, Car Keys and some change. No room for anything else.
When shopping for a dress, there was a model wearing the dress and carrying a handbag. I liked both the dress and bag, so I bought both. The bag carry's everything I need without the fully loaded day bag bulk.
Every Day Carry:
Big, heavy, ugly cross body bag, which has room for Wallet, Cell Phone, Car Keys, Spare Change, Meds, Flashlight, Utility Tool, Folding Knife, Water Bottle, 2-way Radio and other things I might need in an Emergency.
Obviously my shoes and handbag don't match, other than everything is all black.
I now wear slip on athletic shoes all the time. Since I don't go out like I used to, the athletic shoes fill the need for covering my feet, and I have not been anyplace where I might wear heels in years.
Woman have Fashion, Men have a Uniform.
A skirt wearer since 2004 and a full time skirt wearer since 2020.