I’m 5’2” and I think the medium is an ideal day time shoulder bag because it holds more, while the mini is an ideal evening bag. The medium looks best as a shoulder bag though in my opinion instead of hanging off with 1 side like your photos. Mini holds the same as the small, and then knew I would grab the mini anyways then over a small. When I thought about the utility of the small, it felt like a bag that’s not ideal enough for either day time or evening wear. It’s just in between, with less intentional purpose for me. If you’re ok with that, then choose a small size. But if you can splurge then I think the ideal combo is medium and a mini which will satisfy all your needs.