i don't think you should base your purchases on the cost of the purses. if you really adore a purse that happens to be in the print/style and placement you love, then i say go for it. i'd save the money on something i'm not so crazy about and spend it on something i adore (even if you end up spending over retail..). but that's just me..
i have a pirata ciao ciao and i love it, but go with what you love! don't just "settle" for the trasporto ciao ciao, because you'll regret not getting the pirata and might just end up buying both in the long run.
Get the print/bag you love --> Pirata! By the way, I think there is enough black in the print also that it matches not only brown but black.
If you get a bag you're not so crazy about then you end up shelving it away and not really making use of it. Or maybe you can take a chance it will grow on you...Trasporto grew on me. I'm not helping much here am I lol.
Thanks for all your replies! I was going to go out and buy the pirata, but it turns out my bf had actually just ordered me an inferno campeggio off of ebay. So...I'm still debating if I really need two messenger bags.
In addition to that, I found a Vacanze CC that someone on LJ is selling and I absolutely love it as well. xD