I picked up this letter pressed cookie cutter set a little while ago (you can buy it here). It was supposed to be for a holiday party gift exchange, but when I ended up not attending at the last minute I ended up keeping the set for myself. I imagined all of the fun I would have stamping away creating little letter cookies.
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The set comes with each letter of the alphabet, plus "!" and "&". Each character is a rectangle or a square, which you use to cut out the shape. You then flip the cutter over and press the letter onto the dough, imprinting the character. After baking, you can fill the indented letter with icing or leave as-is. Simple, right?
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I made up a basic batch of sugar cookie dough - any recipe will do. My first batch was a total flop. If you don't press the letter hard enough into the dough, the impression will disappear as the cookie bakes. If you press too hard, you'll completely deform the dough and/or cause the dough to rip. My suggestion is to make a few as a test batch and bake them before wasting an entire tray of cookies (like I did).
And although the instructions provide absolutely no detail, I have a hunch that if you pressed the letter onto the dough first and then cut out the rectangle/square shape around the indentation, you would be able to avoid deforming everything. That's my experiment for next time.
Anyway, I managed to get one batch with really good impressions.
After pulling them from the oven, you can see that while they puffed up some, most of the impressions were still fairly deep (with the exception of the letter "s." You know, the one letter I absolutely want to do, as "s" is for "Sadie.").
I then made up a batch of icing. While it is suggested you use royal icing, I don't care for the taste of royal icing. I ended up making something that consisted of powdered sugar, almond extract, light corn syrup and milk. It tasted delicious and the corn syrup ensured the icing was both glossy and firmed up pretty well (not as hard as royal icing, but definitely set up well enough to stack and transport the cookies without ruining them).
Making sure the icing was fairly running, I tinted it different colors and put the icing into decorating squeeze bottles. From there, I simply filled the impressions with icing. All of the cookies that had really good impressions were very easy to fill.
Voila!