It's interesting reading about people worried about wear boots I'm public. Try starting with something short like timberlands or 8 hole dr martens. And work your way up. No one really cares. But you'll feel less exposed
For me I have 4 pairs of timberlands but they don't excite me as such. So I don't feel the same wearing them as a pair of 17 inch engineers. I think the worry comes from people keeping their boot fetish private, which most of us do. That creates a worry that people will see you in boots and you'll get rumbled. But they won't.