I vote for Loop Hobo, because she’s carefree and offers more options to wear with strap & chain. But depends of course of which use case you need the bag for. Let us know which one you pick up!
I love the Loop Hobo bag, and not a big fan of the HR bumbag, so I voted for the Loop. I think it's gorgeous and definitely can be worn crossbody or as a shoulder strap with the chain. Seems to be very functional.
I have the high rise but the loop hobo is still on my wish list. Which one fits your lifestyle more right now? They are definitely for different purposes.