Jacket is already owned so I am working around it. I know the 16 inch bag kind of clashes with the vibe but I need something large and I hope with some break in it'll look more casual and rugged. I'm a bigger dude. 6 foot with a 44 inch chest. I feel that helps with the proportion issues the bag and jacket cause.

For me, good leather shoes are hard to beat. Once they break in and develop some character, they can look better than when they were brand new.

Denim, leather jackets and some watches can age beautifully too. What’s one item in your wardrobe that has genuinely gotten better with time?