Combine 1 cup butter, sugar and egg in bowl. Beat at medium speed until creamy. Add 2 tablespoons milk and almond extract. Continue beating, scraping bowl often, until well mixed. Add flour and baking powder; beat at low speed, scraping bowl often, until well mixed.
Divide dough into thirds. Shape each third into a ball; flatten slightly. Wrap each in plastic food wrap; refrigerate 2-3 hours or until firm.
Heat oven to 400°F.
Roll out dough, one-third at a time, on lightly floured surface (keeping remaining dough refrigerated) to 1/4-inch thickness. Cut with 3-inch round cookie cutter. Cut each cookie in half, using crinkle cutter if scalloped edge is desired. Place each cookie, cut-side down, over lollipop stick on ungreased cookie sheets; press dough lightly around stick to adhere cookie to stick. Bake 6-10 minutes or until edges are lightly browned. Let stand on cookie sheet 1 minute; remove to cooling rack. Cool completely.
Combine powdered sugar, 1/3 cup butter and vanilla in bowl. Beat at low speed, adding enough milk for desired frosting consistency, until creamy. Tint frosting with food color, as desired.
Frost cooled cookies. Decorate as desired. Using white decorator gel, draw 3 or 4 horizontal lines across umbrella. To form umbrella ribs, drag toothpick from top center of umbrella down to bottom edge. Let stand until frosting is set.
Pull out bendable portion of straws to resemble umbrella. Trim straight portion to same length as umbrella stick. Slide straw over stick; trim bent end, if necessary.