Which Outlaw are you considering? I sent back the Outlaw 36 yesterday. On Friday, I will have the medium size Outlaw style no. 38188 that retails for $695 that has a 7 1/2 drop, so the drop is 1/2 longer than the Nomad, for reference. I believe that will fit my shoulder very comfortably. I will gladly take the pictures you are requesting on Friday. Also, there is a reveal of the largest Rogue that retails for $795 here:
http://forum.purseblog.com/coach/outlaw-42-reveal-934781.html. Right now, I have two Rogues in Oxblood and Chalk, but I'm sending the chalk back tomorrow. The Outlaw 36 that retails for $595 is a satchel with a 4 inch drop for hand carry or to carry in the crook of your arm and that one also has a very nice crossbody strap. I loved that strap; it's very comfortable. As for the Rogue, it's a great purse that I love almost everything about, except the price. I personally have never paid that much for a purse. I'm normally a bargain shopper, love to get quality pieces on sale, but I will make exceptions, and since Coach is stating this is a limited special edition that won't go on sale that is one of my exceptions. The Outlaw is also a very nice purse. I'm really surprised there aren't more reveals on TPF. I know a few people seem to have reservations about the gap between the two zippers. On the Outlaw, I think you will really love the turnlock pockets, at least I did, as well as the all suede interior. As for the leather, I'm not sure how I feel about the sheen. I know I didn't like it in the mineral color, but I didn't mind the sheen in the chalk, so I will have to see how I feel about it in the saddle color I ordered. For me, the difference between the Rogue and the Outlaw was with the Outlaw, I felt it was a nice bag, but it wasn't in pebble leather and then I couldn't wear the 36 on my shoulder unless I used the crossbody strap for that, which wouldn't be my preference, and I didn't understand the purpose of that gap...was it just to be unique? But with the Rogue, I immediately loved it. If I were to get picky about the Rogue I could say that the two outside pockets are just open with no clasp and that may eventually bug me, but I doubt it. I do feel they could have priced it at $695 for that size. And I wish the middle section had suede instead of canvas, if so, I don't think I would've questioned the price. But, honestly, when I first saw the Rogue, those few reservations never came to my mind. Well, the price did, but again, I've never paid that much for a purse so naturally it would. As for the weight, I am in the minority but I don't find either bag to be heavy. Now, keep in mind, I am judging it empty. However, I don't carry a lot. I like to have the excess room to add things if needed. A couple people weighed both and I believe the Outlaw 36 is 2.5 pounds and the Rogue is 3 pounds. Let me know if you have any other questions. I don't mind answering them at all. I do think it may come down to you ordering it since you don't have a store near you and then returning it if you're not happy, especially since everyone's taste can vary. Coach has free shipping and free returns and they process returns quickly. I don't live near a store, if I did it would make all of this much easier. But I've processed a lot of returns in my hunt for some nice bags.