Okay, so obviously this is not men's attire. I just took details like sneakers, trousers, button ups, and watches that can be boyish and put them together to give it that cool edge. I loved wearing this outfit.
Button up: Banana Republic similar here
Sweater: Gap similar here
Pants: Forever 21 similar here
Sneakers: Keds buy here
Sunglasses: Forever 21
Purse: Urban Expressions from Stella Laguna Beach
Coat: Forever 21