If you love the style but the straps breaking, you should really consider investing in a quality leather version. Unfortunately those can run very expensive.

As a stop-gap you could look for a removable strap to replace the broken one on your current bag, like this. Just watch how much you’re carrying in it, as the main part of the bag is also only built to withstand so much. You might want to consider a pleather backpack instead, if you’re looking for something sturdy + nice looking that doesn’t break the bank.

My favourite messenger bags are the Proenza Schouler PS1 and the Lowell Dezery, but I don’t personally own either one.

It sounds like we carry a similar load in our bags, but I use a tote instead. I find them more convenient to carry (many have both a long, detachable crossbody strap as well as shorter handles for throwing over your shoulder) and more spacious inside. It doesn’t have a lot of pockets, though, so you do need to organize its contents with pouches etc.