I used to have frozen things in the freezer and would put them into hubby's cooler bag - they would thaw out during the day and stay safe. Other times I would make sandwiches with frozen bread and put various fillings in them. I would be a drink bottle in the cooler. I would 1/2 fill it with water the night before and top up with out the tap water in the a.m. That way he could drink the cold water and it would keep the food cold, too. Another thing I would do was have little pots of yoghurt in the freezer and pop that into the lunch box. Frozen healthy muffins or healthy make-over pizza is good, too. By using this method, you can have a week or more's worth prepared all at one time - then it is just a quick 'grab'n'go' in the a.m :-)
Other things you can do - little can's of things like Tuna, Salmon, Chopped Chicken, etc. and put in a salad. That way it doesn't matter if it gets warmer - it is safe because it hasn't been opened. Make sure that there is plenty of fruit.
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