I'm not sure I have "The Look" either, but I've been riding for 46 years and wear a leather vest throughout the summer when I ride. Take your spouse or a friend shopping sometime and try one on. You might look good in it! I'm sure gbusmech does. Really. Quite sure.Wish I could pull of "the biker look". I ride, and I carry, but you'd never guess I was "That type" if you saw me at the grocery store. I should look into jackets with a carry pocket though. Everyone can pull off a leather jacket look! Well, almost...
Give a "report" on how you like it when you carry and ride.
My first trip to Sturgis was in 1978(dating myself). I lived in Sundance ,Wy and I have always carried..kind of like..a .22 in the pocket is better than a .45 at home..When I was at Daytona Bike Week many years ago (1999 or so) I had a street vendor try to sell me a leather bikers coat. He took great pains to mention the "gun pocket" just inside the right side of the jacket. I gave him the old "why the hell would I ever carry a gun on my bike" look (probably the same look any current anti-gunner would give anyone they just discovered actually CC'd) and just shook my head and moved on. Of course, that was a long time ago when I was a 30-something sheeple type person; before I "woke up". Kinda like the Matrix movie.
I ride nowhere now without carrying - despite all the "Agent Smiths" out there . . . .