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TOMS Skull Slip-On

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Buying the things that we like often brings us immense joy, though sometimes, it also shores up enormous guilt. Blake Mycoskie, founder of TOMS, won’t let that happen to you because when you buy one of his shoes, he also donates a pair to a child in need. For every swashbuckler here in Plunder Guide, this must be one of the best purchases so far. Not only does these slip-ons look cool (brandishing our favorite character ever, Mr. Jolly Rogers), but they look comfy as a step on the clouds. The neatest thing though is the fact that you’ll be helping somebody, somewhere and that feeling is priceless. $95.

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