I can't believe I've read this whole thread and haven't bought a planet box yet! I am such a sucker for lunch boxes.
Right now our favorites are easy lunch boxes and a great, cheap, soft domed insulated "embark" brand box from target that I use with some stainless steal boxes (plastic-ish lids) that I get at Maruki for 1.89 each. I love it that I can fit plenty of food in both of these, along with a water bottle (I have given up on finding an affordable non-breakable double-walled stainless steal bottle, btw, we're using that supposedly safe plastic) and a couple of cloth napkins. We also have an aladdin container for hot foods or soup that I like, though I wish it weren't plastic. And I just ordered a packit lunch bag, which is supposed to keep it's contents "refrigerator cold" for ten hours. We've been having trouble with stuff getting warm and melting. It's so sad when you send some coveted little peanut butter cups in the lunch box as a special treat and they come home all stuck to the inside of a container because they were too messy to eat. :( Imo, it is a little expensive for what it is, but I'll be thrilled if it really works. I also have a nice assortment of silicone cups and picks and cute forks and spoons, and a ton of hand dyed small towels for napkins and some flannel cloth napkins that I made. And then I have a couple of AWESOME asian round stainless "boxes" that have a tray that sits inside (so they're like two levels). I do love them, but they are a little limited because they really need to sit in a box that will be held horizontal, if that makes sense.
We also have a laptop lunch box, but somehow it just didn't work for me. The three compartments of the easy lunch boxes are great, but the four was too much for me to handle somehow. I couldn't figure out how to use the space right. I keep telling myself that that will be true of the planet box, too, because I think they're kind of similar in that respect, but I'm having a hard time believing I wouldn't love that planet box. And I've also got a couple of those sandwich wrap things that I haven't bonded with. I thought I was going to love them, since you can use them as a placemat. (I'm supposed to send two cloth napkins in his box, one for a napkin, one for a placemat, but it's bulky!) But they don't fit around a normal-sized sandwich quite right. They seem more suited to wonder bread-sized sandwiches, I think.
Here's a few pics of his lunches (and you can see a couple of my cool maruki ss containers in there, as well as the round double layered one). I must've put a bunch of these in at the same time, xmas-time maybe? lol Because I NEVER buy ritz crackers, though we all have a weakness for them. And although my kids are completely crazy over kalamata olives, I have only sent them to school with him a few times. So, this is not representative. And, I never do cute stuff anymore, though I do think some about presentation -- colors and such. And I do think a lunch tends to look a lot nicer for some reason if you use a small box and pack it tight, so I try to keep that in mind.
And one more thing... boy can I ever blather on about lunch! 
But, I recently discovered a really nice new lunch food, which is those chicken apple sausages from costco (and trader joe's has something similar). I have a hard time getting Milo to eat protein in his lunch and he loves those. I heat them up so they're browned, but they're cold by the time he eats them. And he actually does eat them. How I wish he would eat cheese or yogurt, though!
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