My 3-year-old just started preschool and I'm packing lunch 5 days a week. I need something that actually keeps the food at safe temperatures but also fits in her cubby and doesn't leak everywhere. She's got a mix of sandwiches, fruit, and sometimes leftovers.
An insulated lunch box with a reusable ice pack is your best bet - something like a soft-sided cooler bag will keep food safely cold for hours and actually fits in a cubby without taking up half the space. Pair it with containers that seal properly (those locking lunch containers work great for preventing leaks) and freeze the ice pack overnight so it lasts through the whole school day.
Soft-sided cooler bags with ice packs definitely work, but here's what actually makes the difference: freeze a wet washcloth or small wet towel the night before and toss it in instead of (or alongside) a regular ice pack - it thaws slower, takes up less space, and you can wring it out and reuse it endlessly. Also stick everything in the coldest part of the bag (usually the bottom) and pack it straight from the fridge in the morning, which keeps temps down way longer than room-temperature containers ever could.
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