First Time Buyer Needs Guidance

I'm 25 and finally ready to buy my first real leather jacket. My dad had an amazing leather jacket that lasted him 30 years, and I want something similar.

I work in tech, so my daily wardrobe is pretty casual - jeans, t-shirts, sneakers. But I also go out on weekends and want something that elevates my look without being too formal or intimidating. I'm not really a motorcycle guy, so I don't need all the armor and heavy-duty features, but I do appreciate that aesthetic.

My main concerns are sizing and break-in period. I've heard leather jackets can be stiff initially and that you should size carefully because they'll stretch over time. I'm 5'8" with a pretty average build, but I tend to layer in winter. Should I account for that when sizing?

I'm also wondering about color choices. Black seems safest, but I've seen some gorgeous brown and tan options that might be more unique. What works best with jeans and casual shirts? And honestly, what's a reasonable budget for someone just starting out? I'd rather buy something decent once than cheap out and regret it. Any advice for a newbie would be really appreciated!