Preheat oven to 325°F.
Cut the butter into small pieces and place it in a large bowl (or the bowl of a stand mixer) with the sugar.
Beat on medium speed until lightened in color and fluffy.
Add the vanilla extract and beat to incorporate.
Add the flour and stir in gently with a spatula or wooden spoon until incorporated. Use your hands toward the end of mixing if you like. Don't overmix, or the cookies will be less tender.
Divide dough in half and shape into two discs.
Dust work surface and rolling pin with flour and gently roll each dough ball into a thin disk, about ⅛ inch, but don't stress.
Using a 2 ½-inch round cookie/biscuit cutter, cut as many circles as you can. You should get between 90 and 100 in total, after you re-roll any scraps and use them to make a few more cookies.
Using a small snowflake cookie cutter (or any small festive shape you like), cut into the center of half the circles. Remove the snowflakes to bake separately.
Transfer cookies to cookie sheets lined with parchment and chill in the fridge for 15 minutes to help them retain their shape in the oven.
Bake for about 15 minutes, until lightly golden around the edges. (Snowflake cutouts may bake more quickly.)
Remove from the oven and transfer cookies to a wire rack to cool completely. Cookies will keep well at this stage for a few days.
The day you plan to present the cookies, spread a nice layer of jam over the flat (bottom) side of each of the intact circles. Heap a little bit of jam in the center and leave a little border around the edge.
Dust the tops of the snowflake-cutout circles, as well as the snowflakes themselves, with plenty of powdered sugar.
To assemble the cookies, gently press a cutout circle onto each jam-covered circle, which should help the jam fill in the snowflake shape and also spread to the outside edges of the cookies.