You know this, and you've apparently experienced this several times. So maybe stop wearing boots when flying? I always carry a pocket knife, but not when flying. Not just because I want to avoid anal probing, but also out of courtesy towards everyone who is behind me in the security theatre queue.

You are assuming they don't need or want the boots for any reason.

I've flow places with 4 laptops before, not because I think it's fun to inconvenience everyone in line, but because I needed them for where I was going.

If I was flying somewhere that I needed boots, I'd probably try to wear them to avoid having them pretty much take up most of my carry on space...

The major difference is that one is basic clothing and the other is something you just have with you. I shouldn't have to buy special clothes to fly. (I happen to own a pair of athletic shoes as well as boots, however, my spouse only owns boots. We don't invest much in clothing).

On the other hand, I don't really find it to be much of a bother. My boots stay on decently without tying the laces and I can usually do a proper lacing when I'm out of the way.

I think only if you have steel caps in Australia as they trigger the metal detectors. I've flown into and out of every major airport in Australia (including OOL) and have only had to remove my shoes when I'm wearing work boots.

I'm pretty sure I didn't take my shoes off when exiting Vietnam. And definitely didn't when traveling from Saigon to Hanoi.