Bentgo or Planet Lunchbox.

Look up retro style metal boxes with him online, that have themes or illustrations that he likes.
Would certainly be a hit with the teachers at least.

LL Bean lunch bag with a Bento box that will fit inside would be a good combination.

My 2 year old has been taking an old tote bag to daycare up until now and I wanted to get him a legit lunch box but he has alot of food and havent seen containers that could fit everything. He really liked to carry the bag himself these days and the tote bag just gets dragged along. Here is what needs to fit: 1. Water straw cup, 2. Milk straw cup, 3. Banana, 4. Plastic box with 3 sections for food- willing to buy something else that would not be so long.

Suggestions? Thanks!