Not totally what you are looking for, but I'd highlghly recommend "Apollo" by Murray and Cox. It focuses on the engineering history of the Apollo program, and it is a superbly well written and researched worked and so many of the stories are about engineering philosophy that I think it'll really be worth your while.
In a similar vein, there's "Skunk Works" by Ben Rich and Leo Janos, which covers the development of the U-2, F-117, and SR-17 aircraft. Not about the philosophy of engineering per se, but it's a great perspective into how problems were solved in a very unique program with extreme goals, before modern computer-aided tools.
