I had a really neat jacket for years and years...I only just started studding it, then it was stolen. So, I recently bought a new one and I am starting over. The leather on my old one was crappy (like everything from Wilson's), but soft - it was WELL worn it. The only way I could find to do it was to rip the liner open and sew it back together
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at first i put cork board under the leather and just hammered my studs in, it worked well but i also ripped my liner open to do it
now all i do is press down on the leather with the stud and the use a really thin exacto blade to make slits where i need to put the stud in.
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If you don't have access to an awl, one can be made simply by inserting a nail into a drill, and then grinding the nail into a sharp round point against an abrassive (sandpaper, grinder stone, the like). Nail can then be held in vice grips and used as an awl. Or you can just buy one in a hardware store for about $5.
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