Price should, but is not always an indication of quality. I usually buy expensive, good quality and stylish shoes, and they generally last several years without any or little maintenance and repairs. I bought a pair of Chelsea-type boots made by Born in September 2006, which I paid $220 at the time. I can wear them with both a suit for work or a pair of jeans on weekends and for travels. I walk a lot, in all kinds of weather, and even after wearing these on several long trips to Asia, Europe, the USA, and everything in between, these shoes are still sharp-looking. Great investment. On the other hand, I bought a $245 pair of very stylish Ted Baker chelsea boots in August 2012. I assumed, given the price and the brand, that I was buying long-lasting quality. I started to wear them casually on the weekend but they started to show wear after a couple of weeks, and the heels wore completely after 2 months. Cost to fix both heels: $42. I would spend that much to fix my Born boots, but it's totally not worth it for these cheaply made expensive boots.