Beginner Seeking Classic Direction

Never owned a leather jacket but decided it's time to invest in quality outerwear. My style is pretty conservative - khakis, button-downs, simple sweaters. Want something that enhances rather than completely changes my look.

Been reading about best leather jackets and getting overwhelmed by all the options. Should I start with something very basic, or invest in exactly what I want from the beginning?

My main concern is looking like I'm trying too hard or wearing a costume. I'm 35, work in accounting, and live in suburbia. Don't want to suddenly show up looking like a different person.

Budget is around $300-400. Is this enough for something decent that won't embarrass me? I'd rather wait and save more than buy something I'll regret.

Climate here is moderate - rarely below freezing but gets pretty windy. Do I need special features for weather protection, or is basic leather sufficient?

Also wondering about break-in period. How long before a new leather jacket feels natural? I don't want to buy something that sits in my closet because it's uncomfortable.

Color preference is probably brown or black, but not sure which is more versatile for conservative styling. Any guidance on making this choice?

Really appreciate any advice from people who remember their first quality leather jacket purchase. What do you wish you'd known starting out?