Oversized leather jackets have revolutionized our approach to autumn and winter layering, and we’re obsessed with how they make everything look effortlessly cool while providing actual room for sweaters and other substantial pieces underneath. There’s something so satisfyingly substantial about wearing an oversized leather jacket—it’s like wrapping yourself in confidence while looking like you borrowed it from someone impossibly cool. We’ve been styling them over chunky knits, hoodie sweatshirts, and even blazers for those days when the weather can’t make up its mind and you need maximum versatility. The oversized silhouette creates this beautiful relaxed energy that feels very current and unpretentious, while still maintaining all that classic leather jacket edge. They’re perfect for creating those coveted ‘borrowed from the boys’ looks that somehow make you appear more effortlessly stylish than if you’d spent hours planning your outfit. We love how they work with both fitted and flowy pieces underneath—the substantial structure of the leather balances flowing fabrics beautifully, while the roomier fit accommodates layers without looking bulky. They’re incredibly practical for transitional weather too, providing enough coverage and warmth for serious temperature drops while still looking intentional rather than purely functional. The styling possibilities are endless—wear them zipped for a more structured look, leave them open for relaxed layering, or even tie them around your waist when the weather warms up. They photograph beautifully in urban settings and somehow make even basic outfits look editorial and thoughtful.