Ready to graduate from my department store leather jacket to something actually worth owning. The difference in quality is becoming more obvious as I learn about leather.

My current jacket was maybe $120 from a major retailer. It looks okay from a distance but the leather feels plasticky and the construction is clearly cheap. After two years, it's showing wear that shouldn't happen this quickly.

Now I understand what people mean by best custom leather jackets and why they cost more. Want to invest in something that'll actually improve with age instead of just deteriorating.

Planning to spend $400-500 this time, which feels like a huge jump but should be worth it long-term. Is this enough for a significant quality upgrade, or should I save longer for something even better?

Fit is my main concern since off-the-rack jackets never seem quite right. Shoulders are usually too wide or too narrow, sleeve length is wrong, or the body is too boxy. Custom seems appealing but also intimidating.

Style-wise, I want something classic that won't look dated in ten years. Learned my lesson about chasing trends with cheaper purchases. Clean, simple, well-made is my new philosophy.

Any recommendations for brands or companies that offer good value in this price range? Especially interested in hearing from people who made similar upgrades.

What quality differences should I expect at this price point versus what I'm used to?