I mostly shoot travel and event (run and gun type stuff), FWIW.
For style, I'd look at the Crumpler bags if I were you. If it were me, rugged and practicality matter because of my locations/subject matter, and nobody is fooled by the fashion bags. Heavy = steal me.
When I'm seriously working the gear, a bag that stands up on its own is worth its weight in gold, so I prefer working out of my LowePro bag that holds 2 lenses side by side.
A slim bag that fits close to the body is worth its weight in gold on
airplanes, trains and busses and I will get out one of my Tenba bags if I have to. I have one that fits my laptop (olive), one that is smaller (rust).
Similar: https://www.bhphotovideo.com/c.....r_bag.html.
I'd be willing to sell you either of my Tenbas for a good price if you are
interested. DM me. I need to downsize my photo bags. I need to downsize my life.
Best advice: buy/borrow a million Gbs of memory cards and don't bother trying to back them up on the road. They are easy to secure and can take a lot of abuse. I would never reuse a memory card on the road unless I could make two separate copies, and that's a lot of gear to tote (laptops and back-up drives, etc.) I would not count on accessing cloud storage in Cuba. So I would just use more cards. Number them, put id stickers on them. A friend in a camera club just found a camera that had been lost by someone else for SEVEN years. They are doing a FB hunt now to find the owner by analyzing subject matter. A sticker would have gotten them their photos already.
Second best advice: order some pet tags as luggage tags. Really loud ones. Put one on your camera where the camera strap connects. One of the most common thefts is to lift the camera in a public place, just waling off acting like it belongs to the thief. They are more likely to pass on something with a tag identifiable at a distance and hard to remove. Mine are rainbow colored and on all my gear: tripod, bags, suitcases. If I could get one on my phone, it'd be there too.
Third best advice: talk to everybody while shooting. The photo becomes a small part of the conversation if you can talk past the camera lens. People like to be shown sincere interest in who they are and will give back some great photos once they see you really engage. You are going to have a blast.
