Styled much like a thicker, longer sports coat, the topcoat originated as a smart outer shell for those wearing a suit. Of course, you can wear it into the office, but if you're looking to lock together a casual look, sport it like Kanye, Gosling and A$AP Rocky—unbuttoned with a solid sweatshirt and some jeans. When the temps drop, pull the coat over a denim jacket or loose cardigan for another layer of warmth. And while you could certainly opt for bolder textures or colors, simple neutral shades provide Olympic gymnast-level flexibility in your wardrobe.

Shown left: $495 by J.Crew