In a large bowl, whisk together the flour, brown sugar, baking powder, and salt. In a separate bowl, mix the egg, almond milk, oil, and vanilla. Pour wet ingredients into dry and whisk until just combined. Do not overmix.
Preheat your waffle maker and lightly grease it. Pour batter into the iron, insert a stick near the edge while still soft, then close and cook until golden (about 3–5 minutes). Transfer to a wire rack to cool slightly.
To make the glaze, whisk powdered sugar, milk, and vanilla until smooth. Adjust consistency by adding a few drops of milk if too thick. Divide into two bowls; tint one pink and leave the other white.
Microwave chocolate chips in 30-second intervals, stirring between each, until melted and smooth.
Dip or drizzle each waffle pop with melted chocolate, then add glaze and sprinkles. Alternate pink and white glazes for a playful party look. Let it set on parchment paper until the coating firms up.
Arrange waffle pops upright in jars or flat on a platter. Serve at room temperature and enjoy these colorful, hand-held treats.