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In our advice column, Ask the Strategist, we take your most burning shopping questions and scour friends, call up experts, and draw from personal experience to answer them. As always, please comment ...

My first fanny pack had legs. Literal legs. It also had eyes, ears, and polka-dotted fur, as it was in the shape of a Dalmatian, presumably one of the 101. This was back when I was too young to care ...