What and how should I look for when choosing a pair of good hiking shoes?

I need a pair that keeps water out and that I can wear both when hiking and through cities (so I don't need to carry another pair).

I'm not looking for a specific brand (although some examples would be welcome), but rather - how do I test whether it's waterproof (before I buy it), how do I know it will be comfortable (I hiked for a day with a pair I got from a friend - they seemed comfortable at first, but then it got really bad - so bad that I lost a toenail after a few days)?

And also - what else should I look for (besides waterproof and comfortable)?

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    This is a good question for chat (if you see someone online, holla!) but shopping recommendations in general are not on-topic on Stack Exchange sites. – Ankur Banerjee Jul 19 '11 at 6:15
  • I think it's probably close to ok, and with a small edit could get there. What hiking shoes should I buy isn't on topic, but this is more about how to learn what shoes are right for you, which should be (as per this blog) – Gagravarr Jul 19 '11 at 8:31
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    Yes - I'm not looking for recommendations, but for tips on what to look for. :) – ibz Jul 19 '11 at 8:37
  • I think it's ok since it's asking what to look for in a hiking shoe. I myself don't know what makes a good hiking shoe. I bought my current ones because they were shockingly cheap and seemed sturdy but I remember wishing I knew how to know if they were really any good or not. – hippietrail Jul 19 '11 at 12:02
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    I've known plenty of people who hike, many of whom can get to a trailhead in less than an hour. You don't have to hike to travel, and you don't have to travel to hike. If it was made less of a shopping question, it might work on our Physical Fitness site. – Dori Jul 20 '11 at 0:24

My general criterion is to look at people who, in their job (i.e. every day during forty years), have the same needs.

For hiking shoes that can be used in city life, I think of soldiers with black leather boots and its associated shoe polish for keeping both nice look and waterproof properties.

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