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Line a baking sheet with parchment paper. Arrange the cookies in a single layer, with the fudge layer facing up.
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Add the frosting to a piping bag fitted with a large round tip. Pipe a dollop of frosting, slightly larger than the Reese’s cup, in the center of the cookie.
12 fudge-stripe cookies,⅓ cup yellow frosting
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Press a Reese’s cup upside down (larger side down) into the center of the frosting, allowing the frosting to seep out and create the hatband.
12 Reese’s miniature cups, unwrapped
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Place an M&M on the yellow band of the hat to create the buckle.
12 orange mini M&M’s
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Place the cookies in the refrigerator for 15–20 minutes to allow the frosting to set before enjoying.