There’s a lot going on here in one watch. The High being that it’s a Rolex, the low is the canvas NATO strap. Interesting contrast because it heavily plays down the Rolex aspect. It arguably could be a good balance between Danger and Play as well. Old Rolexes like this bring up the image of old bomber pilots and their time pieces, but the playfulness of the strap helps tone that down. If you can afford a Rolex, this would be a great way to have some fun with it.
PS. Did you know I do private style consultations? I can help you dress better according to your budget and your needs.