Yeah I have to say that in person I was a bit underwhelmed by the Gabrielle sadly - I was really excited for it but the quality seems a bit so so up close.Since you are asking I vote for the Boy. I like the look of the Gabrielle. I have tried on all 3 sizes of the hobo. I found the small to be cute, but really hard to get in and out of. The large is too big for me. The medium was the best on me (I am just under 5'9). I really like the look and feel of the chains and the cool, casual vibe of the bag. I wanted an all black version and neither of my local boutiques had it, so I did something I have never done, and will probably never do again. I called the Chanel boutique at South Coast Plaza and they had it and I ordered it over the phone. The SA sent me a pic and it looked perfect. It arrived fast, the next day and was wrapped beautifully. At first I loved it, but while inspecting it closely, I saw and felt a pretty deep scratch on the base; like someone had dug their fingernail into the bag. I used the buffing cloth provided, and polished the heck out of it, and though it did soften, the scratch was still visible and I could feel it. I worry that this base is not sturdy enough and I might not have minded as much if I caused the scratch, but since it came to me like that, I returned it. I don't know if I will try again with this bag and would definitely want to see it in person, if I do. Sorry for the long post and good luck deciding!