It always happens but it’s simple to fix
I have a few Horween shell cordovan leather watch straps, as I’ve found them to be the most comfortable leather straps to wear. That’s my subjective opinion, your mileage may vary.
Generally speaking, they last quite a while, over two years with regular wear. That said, I rotate watches somewhat frequently, but I will wear my primary watch three days out of the week at least.
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Inevitably however the lining of the loop that is meant to secure the excess strap will separate from the leather. This isn’t a crisis, but it isn’t very aesthetically pleasing. This has happened universally, to every strap that has received any degree of actual wear.
It would be disappointing, but it’s incredibly easy to remedy. The solution might not immediately occur to some, as the straps are not particularly economical (over $100 USD for a new one) and thus one might be disinclined to go hacking away at them. On a whim at one point, I did just that, and I’ve always been pleased with the results.