As a guy under 40 who is not a douche bag, I would never, ever wear what you are describing. I am currently wearing a white tie dye t-shirt, with a blue 1/4 zip hoodie, with black jeans, and black boots.
You just described a douche bag at Gold's Gym in downtown Indianapolis. Not your average 25-40 man, out for a hike, in suburban Indiana.
I needed this chuckle today. Lol.