longtime lurker here, just posting what I wore today. Been wearing the 5-zips almost exclusively since I've gotten them, imo it looks good with the santiags. Love the slim fit though probably will take it to the tailor to make it slimmer below the knee. Sized down from my regular 29 to 28 following oakghost's advice; a bit tight but not uncomfortably tight. Probably could've got away with even a 27 but they didn't have it available in store. Would definitely recommend the 5-zips!
I feel like wearing a slightly more cropped t-shirt would really enhance your leg and highlight the midwaisted jeans. If it isn't too warm consider adding a jacket. Everything looks better with a jacket.