That completely depends on your style. If you're one to change styles frequently then buying a cheaper pair of leather shoes would be your best bet, and selling/replacing them when needed. However if you find shoes that you could see yourself wearing 5+ years from now and you have your style dialed in then go for the repairable leather shoes. I have a pair of AE (Allen Edmonds) that are legit and I don't worry about them wearing out because I can send them in and get them completely reconditioned for about a benjamin.

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Styles change. A pair of expensive shoes today may look trendy and out of style in 18 months. Buy shoes YOU like at a price you can afford to replace. I like Zappos, www.zappos.com
Many Many quality brands, low prices.

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If you can afford a more expensive better made pair of shoes buy them. They say you should invest money in your bed and your shoes because if you are not in one you are in the other.
Shoe repais can be done relatively cheap ($50-100) and can save you money in the long run if you wear the shoe for several years.
If your style changes a lot you might be better suited buying cheaper "throw away" shoes but remember you can't go wrong with a classic.

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