My 90’s era Fieldsheer road boots are still useful but the velcro closures were tearing themselves off the leather. The leather in the flap area is not particularly thick, certainly not double/triple thickness like the shift patches on the top of the foot. I took a wild guess and picked up a denim needle for the $20 thrift shop Singer.
There are two velcro flaps on each boot for a total of four repaired areas. Each boot has a small tab at the top of the boot (see pic below) and a much larger flap across the ankle.
Started by trimming the edges and loosened bits of the loop material. Since the repair area was attached to a leather boot it was difficult to maneuver and my lack of experience didn’t help.
The final result isn’t half bad. The repairs are strong and the black thread on black leathers hides the unevenness of my stitching.