From my experience in the past with friends who would use me I can say it's time to end the friendship. It's one thing to let a friend borrow money from time to time but it's clear he's taking advantage of your kindness. Don't feel guilty about ruining your friendship because your friend is the one that is responsible for it. It's ultimately up to you on what you're going to do but I would suggest not lending him money and buying him those shoes. If he's truly your friend he'll continue to speak to you even if you stop lending him money. It's good to be kind to people but sometimes you have to realize not everyone in this world is deserving of it.
Is it normal that I'm feeling taken advantage of by my friend?
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From my experience in the past with friends who would use me I can say it's time to end the friendship. It's one thing to let a friend borrow money from time to time but it's clear he's taking advantage of your kindness. Don't feel guilty about ruining your friendship because your friend is the one that is responsible for it. It's ultimately up to you on what you're going to do but I would suggest not lending him money and buying him those shoes. If he's truly your friend he'll continue to speak to you even if you stop lending him money. It's good to be kind to people but sometimes you have to realize not everyone in this world is deserving of it.