 One of the things to know is that you can basically pair a leather jacket with just about any normal outfit you put together, including tailored clothing so long as it's the right leather jacket. Take this look, for example. I've got a very classic and very warm fisherman sweater paired with some charcoal flannel trousers. Simple combination, doesn't rock the boat, but add a leather jacket, throw on some Chelsea boots, and you've given the look a little bit of an edge and made it much more interesting.