President’s Day lands right in the middle of Black History Month, so what better way to celebrate than with some iconic Obama sugar cookies?! Faces can be difficult enough, but portraits are even more challenging since ratios can make the difference between good old 44 and that produce guy in the grocery store.
So when I’m trying to nail a familiar face, I don’t leave anything to chance. There are a variety of different techniques that one might use to do this, but I’m going to zone in on one in particular, and that is stippling. While stippling is generally used to create shading or texture on artwork, we will use it to create guidelines onto a blank cookie.
Start with a blank cookie, bare or flooded. Usually I flood my cookies from icing bottles, but when I’m doing something simple or want to flood cookies quickly, sometimes I will just pipe the border and spoon the flood icing directly onto the cookie.

Make sure the icing is fully dry before you move on to the stippling.

Print a copy of your image, and position it over your cookie. Use the pushpin to stipple guiding points of your portrait onto the cookie. If you are fairly confident in your abilities, you may only need a few guiding points in order to get the ratios correct. But if this is your first rodeo, don’t shy away from straight-up outlining your entire portrait with dots from your pushpin.

I landed somewhere in the middle, with a rough outline of my portrait, and some guiding points for the eyes, nose, and mouth.

From there, you can start piping! It might be helpful to sketch it out a few times on paper but honestly, drawing and piping feel so different that your best bet is to just jump right in.

Keep an image next to your cookie as you are piping to stay on track. Be prepared for differences…embrace them!

Sometimes, they don’t turn out as you anticipated. When I completed my Obama, I stared at him for too many minutes and decided he was a complete failure. Then I went upstairs and took a shower, and when I came back he looked great. Though a little more somber than I expected. So I modified him one last time to have more of a smile. And now I think he looks like he has a Magnum P.I. mustache.


Working with multiple colors can be a little more challenging. You either have to wait for each color to dry or do a lot more freehand. For this next design, I started with a bare cookie.

I did guide points for the darkest color instead of the facial features, which seemed like a good idea at the time.

But once I finished the black portion of the cookie, I wasn’t patient enough for it to dry to do any additional stippling, so it was time to freehand!

At this point, he looks okay, but bears an interesting resemblance to George Washington…which I suppose is appropriate since this is for President’s Day. Fallback plan?

I attempted the left side of his face, but it didn’t look quite right. So I scraped it off. One of the benefits of working on a bare cookie. I waited until the rest of the cookie dried before moving on.

Overall, it’s definitely not my best work, but not bad for a first pass. These were not made for a client, just for fun in celebration of President’s Day and Black History Month, so I’m choosing not to sweat the small stuff. If it were for an official order, I’d have probably done even more guidelines, just to make sure Obama was really on point.

Take care, friends. And keep baking what you love!
[…] recommend, unless the letter is an “easy” one, like M. At the very least, I will stipple a few guide points to ensure that my letters are all of uniform size and […]