Before I start talking about these Uncle Sam Flag Cookies, I thought I would let you know you can make this delicious cookie dough recipe plain—shape it into a couple of logs, wrap, freeze, slice in circles, bake and call it a day. You’ll have wonderfully delicious shortbread cookies. But, if you’re in the mood and would like to take a swing at baking flag cookies, or Uncle Sam cookies, or both, say for Memorial Day, Independence Day, Veterans Day, Presidents Day, Flag Day or any other special day, then go for it and read on!
I baked this recipe twice merely because I wanted to find out how many cookies it could yield if I made flag cookies with all 13 stripes, or smaller flag cookies with fewer stripes. I’ll start here with the smaller flag and Uncle Sam cookies.
I made a few Uncle Sams first, and then made flag cookies out of the remaining dough.
If you decide to make one or more Uncle Sam cookies, shape them first before the flag cookies. If you decide to make only flag cookies, then skip this portion.
- Make the cookie dough.
- Divide the dough into three, tint one part red, one part blue and leave one part plain.
- Between two sheets of waxed paper, roll out some red dough into a rectangular shape.
- Repeat so that you have 3 red rectangles and two white rectangles.
- Stack the sheets starting with red at the bottom, alternating with white and ending with red at the top. Tip: to easily transfer the dough, freeze for about 5 minutes, then scoop it with a spatula.
- Slice the dough into strips.
- From the sliced strips, cut out the trousers and hat. You can download the Uncle Sam template I used here.
- Roll out some blue dough and use the Uncle Sam template for the coat and sleeves. Again, same important tip, to easily remove the shapes, after outlining the shapes with a sharp knife, freeze the sheet of dough for a few minutes. When cold, scoop out the outlined shape with a spatula and the excess dough around it will fall right off.
- Repeat the same procedure to cut out the face hands and shoes. Freeze the different pieces separately in containers until you’re ready to bake the cookies. When ready to bake, piece all the parts together on the baking sheet just like you would a jigsaw puzzle
Here’s how I made the small flag cookies:
- Between two sheets of waxed paper, roll the red dough and then the white dough.
- Cut the rolled red dough into 3 strips, then further slice those 3 strips into 2 to get a total of 6 red strips.
- Cut the rolled white dough into 2 strips, then further slice those 2 strips into 2 to get a total of 4 white strips. Tip: freeze the rolled dough for about 5 minutes to easily move and stack the strips later.
- Take a red strip. Place a white strip on top of it. Separately, stack 3 layers of red and white dough alternating, starting with the red, one white layer in between and ending with a red layer. Slice off about a little less than ½ of the width of this stacked layer of three. Transfer the 3 layers on top of the bottom two layers.
- Shape the blue dough into a square log to fit the space on top.
- Wrap the cookie log tightly in plastic wrap and freeze. Repeat steps 4 and 5 to make a second cookie log, for a total of 2 logs.
- When ready to bake, slice the dough with a sharp knife.
The reflecting pool at Capitol Hill comes alive with Uncle Sam and small flag cookies.
I also wanted to make flag cookies with all the stripes, so here they are. It was a bit of a challenge piping all 50 stars in such a tiny piece of blue real estate, but I crammed them all in there, just for the fun of it. I shaped one tall Uncle Sam first before shaping the cookies.
I got 10 large flag cookies, about 3.5” x 5”, and one tall Uncle Sam, about 9.5”, out of one recipe. I suppose I could have gotten a couple more flag cookies had I sliced them more thinly. The procedure is pretty much the same as making small flag cookies except that you have to slice the rolled dough into more strips.
- In between two sheets of waxed paper, roll out the red dough into a long rectangle. Do the same with the white dough.
- With a sharp knife, slice the red dough into 7 equally sized strips. Slice the white dough into 6 equally sized strips. Tip: freeze the sliced dough for about 5 minutes to easily move them with a spatula and stack them later.
- Stack 6 layers of dough starting with the red at the bottom, alternating with white and ending with white at the top. Separately, stack 7 layers of dough starting with red at the bottom alternating with white and ending with red at the top. Slice a little more than one third off either end of this (7-layer) second stack. Place the 7-layer stack on top of the 6 layers.
- Shape some blue dough into a cube to fit the gap.
- Wrap the assembled dough tightly in plastic wrap and freeze.
- When ready to bake, slice the flag cookie dough with a sharp knife. Shape dough scraps, if any, into stars or hearts.
I shaped the scraps of dough into tiny stars and hearts; they make for good sampling.
This is the same recipe I used in my earlier cookie post. The difference is that those cookies were shaped slightly differently.
The sky’s the limit when shaping these cookies. There really is no right or wrong, just use your imagination and go with whatever pleases you.
- 2 cups unsalted butter at room temperature
- ½ cup granulated sugar
- ½ teaspoon salt
- 1 ¼ cups powdered sugar
- 5 ¼ cups all-purpose flour
- Few drops of red, blue and black gel food color
- Using the flat beater of a stand mixer, cream butter until light and smooth.
- Gradually add the salt and granulated sugar and mix until well blended and fluffy.
- Gradually add powdered sugar and beat until fully combined.
- Gradually add the flour and beat well until the dough leaves the sides of the bowl and clings to the beater.
- Remove about a little less than ⅔ of dough from the mixing bowl. To the dough remaining in the bowl, add a few drops of red food color and beat until color is evenly distributed. Remove the dough from the bowl and set aside. Wash bowl.
- Divide the untinted dough in half. Leave ½ untinted and set aside. Place the other half in the mixing bowl and tint with blue food color. Beat until color is evenly distributed.
- To make Uncle Sam Cookies (TIP: to easily remove the surrounding dough, after sliciing the outline for each shape, place the dough in the freezer for a few minutes. When cold, place a spatula underneath the shape to scoop it out, and the dough will easily separate):
- For the trousers and hat: Between two sheets of waxed paper, roll out a small amount of red dough to make a rectangle. Repeat to make 2 more rectangles of the same size, for a total of 3 red rectangles.
- Roll out 2 rectangles using the white dough, the same size as the red rectangles.
- Stack the sheets of rolled dough starting with the red dough at the bottom and ending with red at the top. Cover lightly with plastic wrap and freeze for about 10 minutes.
- Remove the stacked red and white layers and slice thinly. On each slice, place the template for the trousers and the hat and cut out the shapes with a small sharp knife. Store the cutouts in a covered container in the freezer.
- For the jacket and sleeves. Roll out a small square of blue dough, about the same thickness as the trousers. Place the template for the jacket and sleeve and cut out the shapes. Store these pieces in a covered container in the freezer.
- For the face and hands. Roll out a small amount of white dough and use the template to cut out the face and hands. Store in a covered container in the freezer.
- For the shoes. Take a very small amount of white dough and tint with a small drop of black food color. Use the template to cut out the shoes. Store in a covered container in the freezer.
- When ready to bake, preheat oven to 300°F and line two cookie sheets with parchment paper. On the cookie sheet, piece together the hat, face, jacket, sleeves, trousers and shoes to make the Uncle Sam cookies. Bake for about 18 – 20 minutes.
- Roll out the red dough in between two sheets of waxed paper. Slice into 3 strips of equal width if making small flag cookies, or 7 strips if making large flag cookies.
- Roll out the white dough in between two sheets of waxed paper. Slice into 2 strips of equal width if making small flag cookies, or 6 strips if making large cookies.
- If making small flags, place a white layer over a red layer. Separately, stack a red, white, red layer and slice about a little less than ½ off of the width. Place these 3 layers over the 2 layers. Shape blue dough to fill the gap in the top half, wrap in plastic wrap and freeze.
- If making large flags with all 13 strips, starting with a red layer, alternating with white, stack 6 layers, ending with white. Separately, stack 7 layers starting with red at the bottom and ending with red at the top. Slice a little more than one third off one end and place it over the first stack of 6 layers. Shape blue dough to fill the tap in the top half, wrap in plastic wrap and freeze.
- When ready to bake, preheat oven to 300°F and line two cookie sheets with parchment paper. Slice the flag cookies with a knife and bake for about 18 – 20 minutes.
Uncle Sam Flag Cookies