How to Make the Perfect Cookie Box

For years, Melissa Clark has been on a quest to make the most delicious cookie box to gift to loved ones, logging her triumphs and failures along the way. Here’s what she’s learned.

By Melissa Clark

Eleven months out of the year, I make what would be considered an above average, but not excessive, number of cookies.

But come December, when I pretend my baking obsession is just an expression of seasonal glee, I give myself free rein. Around the holidays, I can legitimize a baking frenzy that, in June, would seem like the flour-dusted ravings of a gingerbread maniac.

While eating the cookies is part of the appeal, so is giving them away, packed by the dozen into tissue-paper-lined boxes. Off they go, to friends, neighbors, teachers, mail carriers — the list is as long as the shortbreads are buttery.

And, pandemic be darned, I plan to continue the tradition this holiday season. Even though I won’t throw a big latke party or Christmas Eve dinner, I can still deliver cookie boxes at a safe distance to my loved ones, a tangible way to spread joy when we need it more than ever.

To keep my yearly baking blowouts at least somewhat organized, I’ve kept a cookie log over the past two decades, noting substitutions, successes and the occasional cookie box failure. (Cardamom in the rugelach is a good idea; adding savory Cheddar cayenne crackers to the box is not.)

The log is also helpful for remembering which cookies I’ve made so I don’t repeat myself too often, and to preserve the recipes for future baking. My goal is always to create a visually stunning cookie box with a balance of flavors and textures that tastes even better than it looks. And over the years, I’ve figured out a way to do it that soothes, rather than adds to, my holiday stress — no piping, no arranging dragées with tweezers, no unearthing rulers or candy thermometers (though I do love a spritzing gun). Bakers should have as much fun making these cookies as their friends will have eating them.

If you’re feeling the urge to make cookie boxes for family and friends, here are my tips for putting them together.

When it comes to cookie varieties, more is more.

I believe in offering a wide assortment of cookies in every box. There’s nothing better than discovering a hidden almond snowball beneath a gingerbread frog. Being enthusiastic, I strive for eight kinds, but three or four is enough to create the thrill.

Every box needs a fruity, jammy note.

Jam-filled cookies like rugelach and honey-roasted peanut thumbprints are study and pretty, and the moisture in the jam keeps them soft for a few weeks. Plus, their chewy fruitiness adds another dimension of flavor and texture.

Recipes: Cherry Rugelach With Cardamom Sugar | Honey-Roasted Peanut Thumbprints

Something sparkly and colorful is a must.

Put these on the top to dazzle when the lid comes off. Think vivid-hued gingerbread painted with royal icing and festooned with sprinkles, or sugar-topped vanilla bean spritz cookies with delicate browned edges that melt in your mouth. Flat, plain cookies like shortbread can rest on the bottom.

Recipes: Sparkly Gingerbread | Vanilla Bean Spritz Cookies

Plan to include something with crunch.

Either a buttery, nubby crunch like a cornmeal lime shortbread, or a nutty crunch, like toasted almond snowballs dusted with lots of powdered sugar, will round out the textures of the mix, making it even more fun to eat. Plus, crunchy cookies are perfect for dunking, which is a necessary cookie box pastime.

Recipes: Cornmeal Lime Shortbread Fans | Toasted Almond Snowballs

A chocolate moment is nonnegotiable.

Whether sprinkled with sea salt, strewn with chopped candy canes, or — as I’m doing this year — crowned with nuggets of white chocolate that caramelize as they bake, brownies are some of the easiest cookies to make, and possibly the most beloved chocolate option. But truffles, chocolate sugar cookies or double chocolate cookies will also get you there. And if you can’t make up your mind, no one will be sad to find two different chocolate cookies cozied up in one box.

Recipe: Black and White Brownies

Pack something for the grown-ups.

Bourbon balls, rum balls, brandy snaps, even mini fruitcakes are perfect for the holidays, and the alcohol helps preserve them, so they keep for weeks. Just warn your friends that some of the cookies in the box may not be kid-appropriate — which will also guarantee there will be something leftover for the adults.

Boozy cookies are my particular favorites to have on hand when all the flour has been wiped off the counters and the sparkly sugar has been mopped from the floor. That’s when I can relax with a bourbon and a bourbon ball, savoring the fruits of another excellent holiday cookie extravaganza — while already planning for the next one.

Recipe: Fudgy Bourbon Balls

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