i just ordered some new bento boxes from j-list and one off ebay.
round totoro bento with miso bowl
this is a fairly unique collectors item! i couldn’t resist. also, i pack a miso soup ball on occasion, so with a small container of rice or onigiri, i think this could work great. he doesn’t like donburi, but i do, so it would work great for that as well.
large rectangular dokodemoissho bento
i hope it’s not too girly for the boy!! it’s a larger size bento in a nice green color, and i like the angles on it.
[edit: he says it's not too girly; he likes it cuz the cat looks stoney, making the bright green color very appropriate.. haha.. furthermore he has ok'ed the use of hello kitty bento accessories in his bentos. i am so glad he is a man who is secure in his masculinity ;D ]
uneri (wave) elongated oval
this looks like a good box for rolled items like sushi pouches, vegetables rolled in beef, or tamagoyaki. i like the dark blue. i’ll need to pack some onigiri or something else in a seperate container for this to be enough food, but i really like the shape.
totoro mini containers
more totoro! i couldn’t resist. one is a little more masculine (as in, not pink) so i think it will work great for salads or fruit or other dessert to add to the lunch.

kakashi bento
i am a super big naruto fan, and when i was looking for bento boxes on ebay, i saw this and couldn’t resist. the seller also has naruto and sasuke boxes. i didn’t get naruto because it’s a little too bright for the kinds of lunches i pack. i think if i was more into decorative bento, i would totally go for it. that and i really liked the design on the kakashi box.

here’s a sample of an assembled bento in the naruto bento series, thought i’d post it just cuz it’s a good example of how to assemble a bento:
