Jessie’s Cowgirl Hat Cookies

With her cowhide chaps and wide-brimmed hat, Jessie sure knows how to dress the part of Woody’s yodeling cohort. Trimmed with piped-on icing for lacing, these red cookie hats resemble the sassy cowgirl’s and make a sweet cap off to dinner or lunch.

Jessie’s Cowgirl Hat Cookies

45 min
10 min


  • Tray
  • Waxed paper
  • Batch of chilled sugar cookie dough (homemade or store bought)
  • Flour
  • Rolling pin
  • 2-inch round cookie cutter
  • Spatula
  • Baking sheets
  • Wire cooling racks
  • Red cookie icing
  • Butter knife or spatula for spreading the icing
  • Large red gumdrops
  • Tube of white decorator’s icing (with a narrow round tip to pipe on the lacing)


  1. Cover the tray with waxed paper and set it aside.

  2. Roll out the sugar cookie dough between sheets of flour-dusted waxed paper to a 1/4-inch thickness. Cut out the cookies and place them on the tray. Then place the tray in the refrigerator to chill the cookies while you heat the oven to the proper temperature.

  3. When the oven is heated, transfer the cookies to a baking sheet. Then bake and cool them according to the recipe directions.

  4. Turn the cookies upside down so the flat surfaces are facing up and then frost them with the red icing.

  5. Once the icing has set, add a top to each hat by slicing the domed top off of a red gumdrop. Then squeeze a quarter size dollop of white decorator’s icing onto the bottom of the gumdrop and gently press it down onto the center of the cookie so the icing spreads around the base and resembles a white hatband.

  6. Pipe a line of trim around the perimeter of each cookie hat brim. Then pipe a series of short lines over the top of the trim to resemble white lacing.

Posted 5 years Ago
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