Flannel Work Shirt

Burkman Bros. Welt Pocket Work Shirt, $198 

A dope shirt jacket is so necessary for cooler weather. Ditch the red-and-black buffalo plaids you'll see everywhere and set yourself apart without looking like a peacock in this grey and yellow rendition. It'll let everyone know you're not the same as all your boys, while still making you look like one of them. Plus it looks as good with jeans and wheat Timberlands as it does with navy chinos and white Jordans.