Classy, comfy and top-notch quality
I have three overland jackets: Jason Bomber, Classic B3 Bomber and Julian Blazer. I love each one! They are each different and are worth every penny and then some. The craftsmanship is perfect; I mean the jackets are simply amazing and the service is also amazing. I expect I'll have all of these jackets for decades.
Jason is even softer (both leather & fur) than the Classic (which is still very soft). Jason is also what I wear when I dress up. It is super warm and the fur is super soft. I prefer to wear Jason when it's 40s, 50s. Whereas I wear Classic when it's ultra cold because it's much thicker (and heavier).
In terms of size, I am on the cusp of medium or large, and I found that the large for this coat is the right amount of room, not overly big and I can easily wear a sweater and not feel like it's too tight.
If you live near a store I highly recommend going there to try on jackets. Their stores are beautiful, and their customer service is top notch.