When in doubt, turn to leather and denim! This has always been and will always be my motto. You can't go wrong with a leather jacket, simple button down and cropped jeans. It's comfortable, but still looks put together. It even has that slight edge to it. Once you have a solid base of simple and classic leather jackets, make a move for detailed ones with things like patches or interesting designs. I love this star patch jacket as it's perfect for layering and the patches aren't large or obnoxious.
While I love a leather jacket with midnight black jeans, sometimes it's nice to do the opposite and switch them out for a light cropped pair. This makes the look more daytime casual. I completed the look with a pair of adidas sneakers and my absolute favorite Ray-Bans (if you haven't noticed, I'm obsessed them).