I recently bought the HH Havana Hobo in Mulberry (I also bought the Tokyo) and love it. Wore it for the first time this weekend and got several compliments.
The leather is very soft and thin so I totally see what you mean about the fact it could show items through it. I found that a little bit but it didn't bother me because its a slouchy, unstructured bag. I love the color, feel, look and price (got it for 25% through LunaBoston).
Here was the review I posted on another forum. I am having problems adding the pictures, think my pop-up blocker is prohibiting me from doing that, sorry!
My first reaction was the same as with the HH Tokyo I got "Wow, this is a nice quality made bag." The leather is soo buttery soft. This is what stood out most to me, how nice the leather feels.
I got the Havana in mulberry. The first picture link (to the HH site) is an accurate pic of the color. I think its a good year around color (esp since its more subued than I expect). IIRC this color is part of their Spring 2006 line. I think this bag would look sharp in chocolate too, black might obscure the detailing.
This is a daytime, every day bag IMO. The shape is nice. It will definitely hold a lot of stuff but slouches well so doesn't look bulky. There is a zipped front compartment that is covered by the flap and a pocket on the back (with a magnent closure). The inside has a pretty colorful flower satin lining (see pic below) and has a zipped compartment and two open pockets in the front. My flip cell phone fits in one of them nicely.
As with the Toyko, no detail overlooked. The bag is put together very well, the stitching is nice and there is nice metal details. The tassle is detachable. On the metal details there is a small " h h" detail, it doesn't stand out (like a logo bag or something) it just adds a classy finished look.
Here are some pics. Some I took from sites cuz they got a more accurate picture than I was able to.