update:
We chose lunchbots. Classic trio 2 and two 8 ounce round leakproof ones. It's worked out really well the last two weeks, but he likes to have a lot of different things versus one or two items. There are many different configurations, and I could add something hot in a thermos jar-apparently I haven't been using it correctly all this time because I've read that they work really well. I also got a set of three small leak proof ones for little things. I wish I had switched to lunchbots a long time ago!
they fit perfectly in the Lands end ClassMate Soft Sided Lunch Box. I got a plain black one to match his backpack, and it clips onto it. He wanted a slim lunchbox, nothing bulky.
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It's time to move on from the laptop lunchboxes, which he has used since preschool! Can you believe it?? I'm wondering what boys take to pack high school lunches. It needs to be leakproof for sure. And reusable. Stainless steel would be a bonus. And what type of bag would they take it in? I'm assuming nothing overly colorful LOL