I don't wear these for a very simple reason, and that is that I feel in some weird way they call attention to my chest. I guess it's the strap crossing through the middle?
I have a long history of back problems so I understand the attraction completely. But, personally, for my back, I vastly prefer backpacks. I have a stylish Kate Spade backpack - it's not as roomy as the one you show from piperlime though. But it gives my back a break, and also leaves me hands-free.
The piperlime one is convertible, isn't it? That is a plus in my book. And the color is lovely. I don't think it's the same as a retro messenger bag. I'd say it is more of a fashionable messenger bag.
Have you tried Coach's ergonomic line? Just a thought. I don't know if that is in your price range, but I can vouch for this line. I carried one of their medium ergo bags all throughout spain for two weeks a few years ago and it performed beautifully. No back pain - but admittedly the bag was on the small side. I don't use that bag so much anymore because of the color, but I might be tempted to duplicate it if for example they had it in a red or yellow or other fun color.
