Cream butter and sugar. In a medium bowl, add ½ cup butter, ¼ cup + 1 tablespoon sugar, 1 teaspoon vanilla, and ¼ teaspoon salt. Beat with an electric mixer for 2 to 3 minutes, until light and fluffy, scraping down the sides of the bowl once or twice. Add the egg yolk and beat for another 30 seconds, until well combined.
Finish dough. Add 1¼ cups flour and beat until just combined. Gently knead the dough twice, then shape it into a smooth ball. Flatten it into a disc.
Roll and chill. Roll the dough between two sheets of parchment paper until it is about ¼-inch thick. Place the dough, still between the parchment sheets, on a baking sheet and chill for 1 to 2 hours.
Prep. Preheat the oven to 350°F and line a large baking sheet with parchment paper.
Cut circles. Use a 3-inch-diameter round cookie cutter to cut out 11 cookies (reroll scraps). Transfer to the prepared sheet pan, spacing them 2 inches apart.
Make wings. Using the same cookie cutter, gently press a curved line into each side of the cookie, about one-third of the way in, to outline the wings. Be careful not to cut all the way through.
Make feather pattern. Using the wide end of a small piping tip, hold it at a 45-degree angle and gently press a series of small indentations inside each wing to create a simple feather pattern.
Make feet. Use the tips of a fork to gently press small markings into the bottom of each cookie to create the owl’s feet.
Make eyes. Use the leftover dough scraps to make two pea-sized balls. Flatten each one slightly and place them side by side near the top of the cookie to create the eyes.
Finish eyes. Press a chocolate chip into the lower center of each eye.
Make beak. Gently press half an almond into the dough directly underneath and between the eyes, with the pointed end facing down.
Bake. Bake for 18 to 22 minutes, or until the cookies are golden brown. Place the baking sheet on a wire rack and let the cookies cool completely.