Mine was a Milt Sparks Roadrunner that was made for a Colt Gov 1911. I ordered it from MS back around 1986-87. Arguably one of the best owb hi-ride concealment rigs ever designed.
The original Roadrunner was designed with the retention band placed around the trigger guard.
Here's what it looked like ....
I liked it so much that I purchased another Sparks Roadrunner for a satin nickle Colt Officer's Model that I bought when they first came out. :)
What was your first premium or custom made holster..?