An oversized leather jacket changes how you wear everything underneath it. The relaxed cut means it works over thicker knitwear without bunching. It reads as intentional rather than accidentally baggy. The weight of quality leather means it hangs properly and creates actual shape even when it is not fitted. A good oversized leather jacket becomes the piece you reach for when you want to add instant polish to a basic outfit. These are the leather jackets in generous cuts that work across seasons and over layering without losing their structure or their credibility.