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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 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.
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