It takes the right amount of skill, pull, swagger, game, juice, whatever you want to call it... to look this GOOD while dressing down.
Many of us guys like to rock a hoodie with some jeans and sneakers an EFFORTLESS template to follow would be Kanye West. The way the clothes come together, each individual and unique item, such as Kanye's BALMAIN hoodie for $932, BALMAIN zip jeans, and fav 'broken-in' Nike Air Yeezy sneakers, is just DRESSED-DOWN PERFECTION.
Doesn't hurt to jazz it up with some wooden accessories and a SWEET velcro strap watch, whatever floats your boat.
If you kinda dress this way, then you're on the right track.