Most likely it means he was checking you out :) Some guys just talk about shoes too however, so see whether it was really just something he said because it is like that or whether he wanted to give you a compliment.
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It means that either 1, she is being nice and complimenting you, 2, she feels sorry for you and is being sarcastic, 3, she is going to steal them in your sleep.
No, not really. It could be way for him to start talking to you, but it doesn't mean he likes you. He likes your shoes, period.
Not necessarily. Some guys may simply be making conversation or have a general interest in shoes. It's important to look at other signals and behaviors to determine if someone likes you.