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Depends what you're going for. Maximizing your financial returns? Possibly.

Not dealing with the hassle of shoe-shopping every 6 months? Totally worth the money.

And time is money too.

Also, get factory seconds and you'll pay WAY less than $500 for a good pair of shoes. I think it was $~200 for me.

How many 30-dollar pairs would such a person have to buy compared to the person who invests in quality upfront? In addition to a quality shoe, it probably also helps to find a competent cobbler who can keep the shoes in good repair to extend their lifetime.

By my back of the envelop calculation, as long as its less than 25 shoes over 10 years, stock market is the winner.

Where Allen Edmond shoes are the real winner is compared to the shoes a level or two below them. Like Cole Haan. They last a lot longer but only cost twice as much.

My 30 dollar dress shoes have lasted 15 years, since I rarely wear casual dress shoes.