Having a major dilema, please help!

For the holidays i wanted to add a black leather bag to my collection. i wanted something quirky and different, definetly at least shoulder length, and besides that i didnt really have any specifications. i just want something that i can invest in and count on being a great, cool bag for years to come. Now im having a huge problem deciding! I purchased this chloe vachetta hobo in black for a pretty good sale price, but its still pretty expensive. I was also looking at the Botkier nomad satchel. I think im having such a hard time figuring it out because i dont really have anything specific in mind, and both of these bags are so different! I love the chloe and it would be hard to part with it, but i dont want to keep it unless its really going to be worth it. Does anyone have some words of wisdom? or even some others to consider that would be even better? thank you so much! here are the pictures

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I just bought this Botkier last night in Bronze. It is quirky, isn't it? I hope I like it when it comes...but then again, I LOVE ALL Botkier bags. They are fast becoming my new favorite. My Cleo wrapped up under the tree is nearly killing me!