New leather gear is stiff and squeaky. It will soften with wear, but it takes a long time. You can try rubbing in mink oil or some other leather dressing to soften it up. Sometimes it will soften a bit if it's damp--not wet. In the short run, you can force the end through the buckle with pliers, but be careful not to mark the exposed portions. Some rubber tubing places over the ribbed portions of the plier jaws will help protect the leather.
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