The bag situation is pretty easy to explain. Packs that seem to work in the store can be awful at the end of long day of an 8 to 10 mile hike with photo stops. Why? Well, I found that my torso length is short, close to child-sized, and that the only packs that carry more than 5 pounds well (and I hike with about 4 pounds water and some other "10 essentials" stuff) are hiking/camping backpacks that are both sized and adjustable within that size range (women's extra-small to small). So, I need to get the photo-specific also-ran packs onto the photo club email list for sale. Now I have three sizes of panel-access hiking pack (25, 38, 55 liter) and 4 sizes of padded inserts, plus a super-reliable dry bag duffel with padded liner for kayak/canoe. The packs also serve as ordinary luggage - 25 liter pack fits under airline seat even in regional jets and between legs in 4 to 12 seat puddle-jumper prop planes, so the camera / 2 lenses / laptop is directly in sight at all times, and I don't have to sweat about getting an overhead bin. For casual walkabout use where the bag is on the ground more than on the shoulder, I have a used Domke bag bought from another photo club member who moved to Fuji and got smaller bag.
If my back or shoulders hurt, I am not happy. Fashion isn't a huge issue, I just try to find packs in any muted dark color.