Thanksgiving cookies of Pilgrim shirts and hats. An easy step-by-step tutorial by Semi Sweet Designs

Decorated Cookies

Thanksgiving Cookies – Pilgrim Shirts and Hats

Written by Mike Tamplin Nov 7, 2013

70 Comments

With Halloween over and daylight savings time ended, it really feels like Fall is in full swing. Unfortunately, here in the Pacific Northwest we had a horrible wind storm a few days ago. Now all the autumn-colored trees are prematurely bare and the leaves are a mushy mess on the sidewalks.

Mushy leaves and shorten days aside, this season is still my favorite time of year. Plus, we are fast approaching my favorite holiday, Thanksgiving! Since the holidays can be hectic, here are some relatively easy Pilgrim Thanksgiving cookies ideas to make for the upcoming event.

Pilgrim Shirt Cookies

Preparing the Dough

These pilgrim shirt cookies use the same general idea as my Irish shirt cookies I made for St. Paddy’s Day this year. I used the present cookie cutter again from this Wilton set to make these shirts.

wilton present cookie cutter

The Icing Process

  1. 1

    With warm brown piping icing, outline the edges of the cookie and add a collar detail at the top. Take flood icing and fill in the middle. Leave the cookie to dry completely.

    pilgrim shirt cookies step 1
  2. 2

    After the cookie had dried and hardened, take a food marker and a circle cookie cutter to mark a half-circle guide line that touches the two top corners.

    pilgrim shirt cookies step 2
  3. 3

    With white icing, outline over the marker line and across the top collar as shown below. Pipe a line down the middle. Next flood just one half of the white section. Leave this cookie to set.

    pilgrim shirt step 3
  4. 4

    With black piping icing, outline a belt rectangle near the bottom of the cookie. Then flood the belt with black flood icing and finish the other half of the white section with white flood icing.

    pilgrim shirt cookies step 4
  5. 5

    For the final touches, add a belt buckle with gold 15-second icing and a bow tie with black icing. Ali Bee’s Bake Shop has a great tutorial on how to pipe a quick bow out of icing.

    pilgrim shirt cookies step 5

Pilgrim Hat Cookies

Preparing the Dough

To accompany the pilgrim shirt, I made hats to complete this Thanksgiving ensemble. There are pilgrim hat cookie cutters available (which you can find here or here to name a few) but I don’t happen to own one. I just repurposed the same cupcake cutter that used for my skull candle cookies by trimming off the candle part.

pilgrim hat cookies dough

The Icing Process

  1. 1

    With black piping icing, outline the bottom half of the cookie and add a square shape top. The outline should resemble an upside-down piece of toast. Take flood icing and fill in the middle. Leave cookie to set.

    pilgrim hat cookies step1
  2. 2

    With white piping icing, outline a arched band as shown below then fill the middle with white flood icing. Give the white icing time to set.

    pilgrim hat cookies step 2
  3. 3

    Lastly, add a buckle with gold 15-second icing and add black outline details around the cookie as shown below.

    pilgrim hat cookies step 3

I’m not sure what actual pilgrim outfits look like. These Thanksgiving cookies are my loose, simple interpretation of a few different references I saw online. I opted for a brown shirt instead of the common black you might see most often just to introduce another color into this mix. Although, I think a gray or navy blue shirt would have worked well, too.

Thanksgiving cookies of Pilgrim shirts and hats. An easy step-by-step tutorial by Semi Sweet Designs

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70 replies on “Thanksgiving Cookies – Pilgrim Shirts and Hats

  1. Hi Mike,

    Love these! What icing recipe do you use? Thank you

  2. Newbie here!!! Love your tutorial on this.. so simple… Made them and received lots of compliments. Thank you for sharing, and I look forward to copying your creativity! :)

  3. As the owner of hundreds of cookie cutters I get such kick out of seeing how you repurpose your cutters! Love it!! and very innovative!

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