Use a cobbler's simple rule to determine whether your shoes are worth the money to repair
Alex Plishtiev, the owner, took one look and quoted me a price: $20.
I hesitated. The shoes had only cost $20 to begin with.
Was it worth it?
"It depends if you like the shoes," he said, and then explained his simple rule:
"If the upper part of the shoe dries out or starts cracking, then it's not worth repairing. But if the uppers are fine, the bottoms can always be fixed."
The same thing holds true if you're talking about a $100 pair of shoes.
Once the uppers - meaning anything that isn't the sole - go, that's a sign that the shoes have truly reached the end of their life.
You may think that you're saving money by paying $50 to repair them instead of buying a brand new pair, but they'll likely need more, equally expensive repairs before long.
If the soles are ruined, on the other hand, that's easy to fix.
A repair in the range of $20-$30 can give them several extra years of life, and leave you feeling like you have a brand new pair of shoes. That's why finding a good shoe repair shop is a simple and easy trick for saving money. You can see Business Insider and Yelp's ranking of the best shoe repair shops in New York City here.
Of course, some people choose to ignore this rule and repair old, broken-in shoes for sentimental reasons. Plishtiev showed me a pair of cowboy boots that he'd patched up to hide giant holes in the leather. "The repairs on these cost $125," he said. "But the owner loves them so much that he wanted to keep them."