Hi sococalifornia!
If I were you I would go for the Taïga Kasbek (since you like totes... but they're really not my style)... But I don't know about it, because you're 17 and Taïga looks a bit too "executive-ish"... Why don't you reconsider about messenger style bags? Among the manly bags suitable for your age (and mine) I think the messengers are the best. Or other small bags, like Damier Geronimos or something like it... OR my favourite damier bag (yet I still didn't had the guts to buy it), the Broadway. I think it is perfect. It's not just "another" messenger bag.. It's classy and trendy at the same time.. And you can wear it now and in 10 years... Pretty much like the Utah messenger. But that's just MY opinion, according to my taste... You have to decide for yourself and not just buy whatever people tell you to.