Add the sugar and butter to a large mixing bowl and beat at low speed until light and fluffy, about 3 minutes.
Scrape the sides of the bowl. Add the almond milk, vanilla extract, and food coloring, and beat together for another minute.
Add the dry ingredients to the bowl and mix until the cookie dough comes together. It will be a bit dry, but you should be able to pinch it and have it come together. If the dough is too dry, add a tablespoon of water.
Divide the dough evenly into two parts. Bring together to form a disc, flatten, wrap in plastic, and refrigerate for at least 1 hour or overnight.
Line two baking sheets with parchment paper.
Lightly flour a cutting board and rolling pin. Remove one disc of dough from the fridge, unwrap, and knead it on the cutting board for 30 seconds – 1 minute until it is pliable.
Sprinkle the top of the dough with more flour and roll it out until it is about ¼" thick.
Use a round 2 ½” cookie cutter to cut out your cookies, then use a smaller “heart” cookie cutter to cut out the center “window” of each cookie.
Transfer each cookie to the baking sheet, leaving at least ½" of space between each cookie. Repeat with the remaining dough, dusting with more flour if necessary. Each disc of dough should make about 15 cookies.
Place the cookie sheet back in the refrigerator to chill for another 30 minutes.
Remove the second disc of dough, and repeat steps 7 and 8. Cut out the dough using the circular 2 ½ inch cookie cutter, but do not cut out the center, these will be the bottom of the sandwich cookie. Place these cookies in the refrigerator to chill for 30 minutes.
Preheat the oven to 350°F. Bake each baking sheet on the middle rack for 8-10 minutes, until the bottoms of the cookies are light brown.
Cool the cookies on a wire rack. While the cookies are cooling. Whisk together the powdered sugar and remaining matcha powder.
Dust the top of the cookies with the hearts with the matcha powdered sugar.
Assemble the cookies. Spread ½ to 1 teaspoon of raspberry jam on the bottom cookie. Top with the cutout heart cookie.
Store in an airtight container at room temperature for up to 5 days.