In a food processor, whirl flour, sugar, and salt. Add butter and pulse until pieces are almond- and pea-size. Sprinkle 1/4 cup plus 2 tbsp. ice water over mixture and pulse 3 or 4 times just to distribute.
Dump mixture into a mound on a work surface. Working quickly so butter stays cold, firmly press dough with heel of hand, pushing dough outward from center. Scrape dough from work surface using a bench scraper, and toss to redistribute wet and dry patches. Repeat, pressing on dry patches and tossing to create a soft dough with no dry spots. Don't overwork; you should see pieces and streaks of butter.
Divide into 2 portions and gently press each into a 3/4-in.-thick disk. Wrap each in plastic wrap and chill until firm, at least 2 hours and up to 2 days.
Unwrap and lightly flour first pastry disk, work surface, and rolling pin. If dough is too firm, let stand about 5 minutes. Working from center with short strokes, roll pastry into a 12- to 13-in. round that's an even 1/8 in. thick. As you work, lift round, using a bench scraper, and reflour board and pin as needed to keep it from sticking.
Fold round in half and open up into a 9-in. pie pan, easing it into place without stretching. Trim overhang to 1 in.
Roll out second pastry disk the same way as the first to an 11-in. round. Cut shapes close together with a floured 2 1/2-in. cookie cutter. Transfer to a baking sheet. Gather and reroll all scraps and cut the same way (you'll have about 25 cutouts total). Chill cutouts until firm, 15 minutes.
Make ahead: Up to 1 month, frozen airtight.