Clothespin Cookies

Why You’ll Love This Recipe

I love that these cookies feel like a throwback to old-school baking, but with a modern creamy twist. The pastry is buttery and crisp, and the filling is smooth, rich, and fluffy. They do take a little bit of time to make—but most of that is chilling and cooling. The actual steps are simple and satisfying. And the result? Totally worth it. They’re beautiful, crowd-pleasing, and irresistibly good.

Ingredients

(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

For the Cookies
½ cup unsalted butter, chilled
2 teaspoons granulated sugar
1 egg yolk
1 ¼ cup all-purpose flour
1 dash salt
5 tablespoons water

For the Filling
¾ cup granulated sugar
¼ cup flour
1 cup milk
1 cup unsalted butter, room temperature
1 teaspoon vanilla extract
1 dash salt

Directions

Cookies

1. I start by adding the butter, sugar, egg yolk, flour, and salt to a food processor and pulsing everything together. Then I add water and pulse again until a dough forms.

2. I transfer the dough to a floured surface and press it together until it’s just tacky (not sticky). I divide it in two, wrap each half in plastic, and chill in the fridge for 1 to 2 hours.

3. Once the dough is almost done chilling, I preheat the oven to 375°F (190°C) and wrap my clothespins in small sheets of foil.

4. I roll out one piece of dough into a 12×8 inch rectangle, trim the edges, and cut it into 1-inch strips.

5. I wrap each strip around a foil-wrapped clothespin, making sure the dough overlaps slightly. I place them seam-side down on a parchment-lined baking sheet and repeat with the second dough half.

6. I bake the cookies for 18–20 minutes, until lightly golden. After cooling them for 2–3 minutes, I gently remove the clothespins and let the shells cool fully on a wire rack.

Filling

1. In a saucepan, I whisk together the sugar, flour, and milk over medium heat until it thickens like pudding (about 10 minutes).

2. I transfer the mixture to a bowl, cover it with plastic wrap touching the surface, and chill it in the fridge for 40 minutes.

3. In the meantime, I whip the room-temperature butter with a whisk attachment in a stand mixer for about 8 minutes until light and fluffy.

4. Once the flour mixture is chilled, I add it one scoop at a time into the butter while mixing, then switch to the paddle attachment.

5. I add vanilla and salt and beat the mixture on medium-high for 10–13 minutes until smooth, fluffy, and pipeable.

6. I fill a piping bag fitted with a star tip and pipe the cream into the cooled pastry shells.

Servings and timing

This recipe makes 12 cookies.
Prep Time: 1 hour
Cook Time: 20 minutes
Chill Time: 2 hours
Total Time: 3 hours 20 minutes

Variations

I love playing with different flavors and textures:

• I sometimes add a teaspoon of almond extract or orange zest to the filling.

• A dusting of powdered sugar before serving gives the cookies a classic finish.

• For a chocolate twist, I stir in a little cocoa powder or melted chocolate into the filling.

• If I want to make them look extra fancy, I dip the ends of the shells in melted chocolate and sprinkles before filling.

Storage/Reheating

I store filled cookies in an airtight container in the fridge for up to 3 days. They taste best the same day, but they hold up well if I keep them chilled. I don’t recommend reheating them, but I do like to let them sit at room temperature for 10–15 minutes before serving to soften slightly. If I’m making them ahead, I keep the shells and filling separate and fill them just before serving.

FAQs

Can I make the dough ahead of time?

Yes, I often make the dough a day in advance. I just keep it tightly wrapped in the fridge until I’m ready to roll and bake.

What can I use if I don’t have clothespins?

Metal cannoli molds or small oven-safe dowels wrapped in foil also work. I just make sure the shape allows the dough to be removed easily after baking.

Can I freeze the cookie shells?

Yes, I freeze the unfilled shells in a sealed container. When I’m ready to use them, I let them thaw at room temperature before filling.

Can I use store-bought puff pastry instead?

I can, and it saves time! I roll it out, cut it into strips, and follow the same wrapping and baking steps.

How do I keep the shells from breaking?

I let them cool just slightly before removing them from the molds, then cool completely on a wire rack. If I try to remove them too hot or too cold, they’re more likely to crack.

Conclusion

Clothespin Cookies are a charming, old-fashioned treat that always gets attention and rave reviews. With their crisp golden shells and fluffy vanilla cream, they’re the kind of dessert that feels both elegant and comforting. Whether I’m baking for a holiday tray or just indulging in a baking day, these cookies remind me why I love homemade sweets so much—they’re beautiful, delicious, and made with care.