A cuff ain't a roll. You get a sewn cuff on your trousers, they're going to work with anything you throw at them. If you roll them up, as you have there, then you're limiting yourself to super casual stuff.
The leg openings on those trousers are too small for those boots, too. You may have big feet, in which case you'll want proportionally wider trousers. They may just be big, clunky work boots.
I'd press the trousers, and wear them with more-refined shoes, and then you'd be more-or-less set. That said, the next navy blazer you buy should be more casual: smooth worsted and delicate pic-stitching means that one's never going to be as much at home with chinos as a hopsack/fresco blazer.