If you’re building a holiday cookie box, the secret isn’t making one perfect cookie—it’s making a mix of textures and flavors: something chocolatey, something buttery, something crunchy, something chewy, and at least one “wow, those are adorable” cookie. This collection does exactly that with six crowd-pleasers you can bake (or assemble) in stages, store easily, and share without stress.
You’ll find:
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2 Hershey’s Kiss cookies (one chocolate, one vanilla-candy-cane)
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Classic Peanut Butter Blossoms
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Coconut Macaroon Kiss Cookies
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Christmas Kitchen Sink Cookies (loaded, chunky, chewy)
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Chocolate-Dipped Oreo Truffles (no-bake and always first to disappear)
Before you start (cookie-box success tips)
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Bake in batches: Make doughs first, bake the next day. Most cookie doughs chill well for 24–48 hours.
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Use parchment paper for easy cleanup and consistent browning.
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Cool completely before storing or you’ll trap steam and soften the cookies.
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Separate strong flavors (peppermint + peanut butter) in your cookie tin using cupcake liners.
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Freeze what you can: Truffles and baked cookies freeze beautifully for 1–2 months.
1) Chocolate Peppermint Kiss Cookies (Crinkle-Style)
Fudgy chocolate cookies topped with a striped candy cane Kiss—holiday magic in one bite.
Yield: ~24 cookies
Oven: 350°F / 175°C
Time: 15 min prep + 10–12 min bake
Ingredients
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1/2 cup (115 g) unsalted butter, softened
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1 cup (200 g) sugar
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1 large egg
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1 tsp vanilla extract
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1 cup (125 g) all-purpose flour
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1/2 cup (50 g) unsweetened cocoa powder
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1 tsp baking powder
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1/4 tsp salt
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1/2 cup powdered sugar (for rolling)
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24 Candy Cane Hershey’s Kisses (unwrap before baking!)
Instructions
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Cream butter + sugar until fluffy (2 minutes). Beat in egg + vanilla.
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In another bowl, whisk flour + cocoa + baking powder + salt.
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Mix dry into wet just until combined. Dough will be soft.
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Chill 30–45 minutes (helps prevent spreading).
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Scoop 1 tablespoon dough, roll into balls, then roll generously in powdered sugar.
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Bake 10–12 minutes until puffed and crackly.
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Immediately press a candy cane Kiss into the center. Cool on the tray 5 minutes, then move to a rack.
Pro tip: If your powdered sugar “melts in,” double-roll the dough balls: once before baking, then a quick second roll right before the oven.
