Ha ha slowly it came to that yes. I own one pair of Levi jeans (my waist fluctuates too much and my social calendar demands none of it so I just don’t keep more than one) which I rarely use (tropical country now). Only gym and running shoes, I’m a sandals guy. Of course this changes when I’m in New York in winter but I still just have boots and that same single pair of jeans I suppose.

Well I don't know New York but in a proper pub they will be fine with whatever trousers and shoes you have. For that matter I once walked into a country pub (not one where they know me) in only wet swimming trunks and we persuaded them to serve us on credit.

That's exactly what I'd wear to a pub, bar, restaurant or cafe so not sure why you'd think that would be an issue. Even most nightclubs don't bother about dress codes much these days.

I’ve been turned away twice in my life for not wearing shoes, and once for not wearing pants. So thats something?

The clothes are the legally justified excuse, really they’re going by their impression of you.