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Back in the day when I was a young impressionable dumb kid, I bought a pair of $180+ Timberland Boots which are completely useless to me now in the place I currently live.
But my best purchase ever was buying a pair of brand new $220 Black Italian Leather Boots for only $20 from Banana Republic. I still use them to this day & they are the most comfortable pair of "dress" shoes I have ever worn.
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