Sorry Artificer, I have to disagree that Docs are too "Tartan Army". I wear them sometimes when going in for a more relaxed style, say with a jumper (pullover) in winter or a polo shirt in summer. I think they are far more preferable to the sport shoe, runner look that seems ever present these days.
I would align them with the hiking boot look and with scrunched down socks, I think they look good. And this is from a person who prefers to dress in a traditional manner most of the time.

I think the OP looks great for a night out on the town