Generally I'd say you up the formality of the pants before adding a tie. When I was younger I wore ties more. In retrospect this is because I was poor and lacked the right clothes. I like jeans/shirt/blazer, from there you'd go nicer pants/shirt/blazer -> suit/shirt -> suit/shirt/tie ... normally. or instead of suit/shirt, sportsjacket/pants/shirt/tie.
If you really want to do it though, you need a casual looking -tie-. Mr Sutherland's looks odd because its a very formal tie. First guy has loose tie which I wouldn't do at my age trying to dial formality down. Like I said, I wouldn't wear the tie with jeans generally (though I've worn sweater/tie/jeans) but if doing it, I wouldn't wear a standard silk tie.
I'd either go with a silk knit tie, or a wool tie, something like that. Even a slubby raw silk. You can pick up cheap knit or wool ties at tiebar.com btw.
If I wanted to splash it up I'd probably go pocket square no tie with that look tbh.