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It's only possible to effectively "put yourself in another person's shoes" if you have previously experienced their situation.

If you are just imagining what their experience would be like rather than referring to actual past experience, you will be prone to error because it would come down to how good your imagination is at representing their reality.

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That's very true, but it's still infinitely better than never making an effort to see anything from the POV of others. Most things in life that are worth doing fall into the category of things where you're constantly trying to attain some unattainable ideal, like always being rational or ethical or having a healthy lifestyle. Making the effort is far more important than scoring 100% on it.

Also, if someone never makes that effort, they will never even begin to understand and internalize the degree to which they're biased by their own perspective and experiences.

You'll be prone to error, but it's not impossible to gain perspective through analogy and empathy.

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