I know a guy that once said more than once:
“find what works and wear it into the ground”
This has kinda sorta been my philosophy on clothing as well as bike parts and or bike clothing and bike maintenance too. There’s some trial and error in there and learning from experience. The ensemble or getup I wear to work every day is 90% thrift store scores that have taken a while to accumulate sprinkled with a few key new items. Multiple layers in the winter and dependable things year round. When I was an Elliott Bay Messenger I had a polypro long sleeve baselayer that I wore until the entire back wore out to nothing at all. I ignored the threadbare patches until it just fell apart. I still have a pair of double front tights that I had when I worked downtown over 10 years ago. When I find something that works I wear the shit out of it until I can’t wear it anymore and then I have a hard time finding suitable replacements.
I don't believe you can just walk into REI and purchase the perfect outfit. I'm sure you've seen those that try. Just as you cannot replicate the smell of a messenger. Authenticity is earned.
I’m in the process of ordering my 4th Double Darn cap. I prefer the Hunter Cap in an understated dark thin winter wool which works 9.5 months out of the year here in Seattle. A cotton cap is great for the Seattle summers. My current Double Darn cap has been worn day-in-day-out so much that my helmet has worn a hole in the forehead.
Misia makes a fine cap. She can custom make them too if you have a big head like me. My old lady has a couple Double Darns and Junior Junior and Junior have been through a few too.