Chuck Taylor's for 5 years straight, and the sole is very large and extends past the toe and behind the heel of your foot quite a lot. Also, they take about 3 weeks to a month to break in, and during that time the leather is very stiff (walking up and down stairs for the first month in these was a hazard). All in all, if you can put up with the comfort issues that come with wearing these for a month of breaking in, they're definitely worth it.
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