We all wish we could skip this step, but even the Queen of England is known to hire women to wear her new shoes first before she does.
How long it takes to break into your new leather shoes will depend on the construction of the welt, the fit, and the leather used. Blake stitched shoes will normally take less time than Goodyear welted shoes because the sole is much thinner, but Goodyear welted shoes made of full grain calfskin from Italy or France takes on average a day or two of wear before the leather softens and starts to mold to your feet. If shoes don't get more and more comfortable after this period of time, then the problem lies with the fit of the shoe.
As long as the fit of the shoe is correct, it always helps to apply leather conditioning for the first time since the shoes have been made to properly replenish the leather with its adequate moisture so it regains its softness.
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