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I've found that leather does become pliable over the years. This happens faster if the leather is thin. Thick leather holsters seem to last longer as do those with a double thickness around the holster mouth. Better yet, some even have a metal insert between the leather pieces around the mouth to help it hold its shape.
I've seen ads for holsters that use kydex on the inside and leather on the outside.
Speaking of which, you might give a Kydex holster a try. They never lose their shape or stiffness, unless exposed to powerful solvents or hundreds of degrees of heat, in which case holster stiffness is the least of your worries, especially if you're wearing it at the time :lol:.
You didn't mention if you have a belt or IWB holster, and this could make a big difference. Kydex might be too stiff for IWB use.
Hope this helps.