I too have been there and done that, in the air AND on the ground. I'm all for the the best equipment, but I've wore 3 different utility uniforms, not including a flight suit, during my 28 year career. And each time we changed styles, it cost more to buy the new uniform. Yes, once you are out of basic training, you must buy your own uniforms. Enlisted trrops get a uniform allowance, but it's not enough to buy new uniforms, so it takes money out of their pocket. Officers don't get an allowance, they just have to buy them.
When you're in a combat area, you can get a new uniform at no cost if you need it, but it makes a lot of administrative headache for your commander and First Sergeant, but that's what they get paid to do.
Don't even get me started on the dress and service uniforms.