Suit Jacket (maybe a worn in corduroy blazer, simple classic blue blazer. Something tweedy, maybe a heavy chalkstripe flannel. in the summer a tan linen sportcoat Shirt - university stripe shirt, oxford shirt, something like that tie- repp tie, or something thicker in the winter jeans - old 501's, NOT tight. if not the levis, something normal, that a 30-50 year old man can wear and not look absurd shoes - chukka boots, in suede or brown calf. maybe a pair of heavily brougued oxfords, double leather soled.
Yeah, that could look all right. Not highrise, tapered jeans though. A straight fit (not "relaxed" fit) jeans with a low-medium rise (just under the waist, but not hanging off the hips) would look just fine. Still, the shirt should be fitted, and now that I think about it, of a rougher cloth (like an oxford cloth), not ironed to perfection (I would recommend a soft, slightly out of shape collar) and not all sleek and Dolce Gabbana'd. And definitely, the jacket should be slim and of a rougher cloth. No boxy jacket. Chukka boots would go great. Shabby chic works. If you're going for this look, don't be too anal about it. It is a weekend look, after all. Guy number 1 can look alright, but is very likely trying too hard. If he has lots of hair product and looks all gym toned, he may as well be in an ad for Tom of Finland.