I’ve always wanted to do Christmas cookie boxes, but it wasn’t until last year (2020) that I finally started doing it! It’s a surprising expense and finding the cute supplies for everything is tricky. Last year I definitely did a better job of wrapping everything up—and actually shipping the boxes out. This year, due to our new oven I had complications (more on that later) which made shipping boxes out on time impossible, I only ended up hand delivering mine. But I hope next year to get back to shipping these out!

How I choose what to bake

I have a few personal favorite Christmas cookies I love to bake, but a cookie box is not just about me. If you’ve given cookies away or sent a cookie box before, it can be helpful to ask what people’s favorites were. I usually then take the greatest hits, my traditional cookies (the ones I make every year), and then try to add in a few recipes that I may not love, but that diversify the cookie box so it’s not all one flavor. I also try to choose cookies that can ship well without breaking. This year due to my oven debacle I didn’t get to add as much variety as usual because I wanted to make like, seven types, so next year I hope to try to branch out more!

Usually I would suggest doing something like:

One sugar or butter cookie
One spice cookie
One chocolate cookie
One peppermint cookie or flavor
+ whatever else!

Because I wanted to try peppermint bark this year, I ended up doing two peppermint chocolate flavors. But alas! It’s my favorite holiday flavor combo and both were hits.

What I baked

Chewy Molasses Spice Cookies

Dessert Person by Claire Saffitz

Where do I begin with this recipe? It’s perfect and it’s perfect every time because the recipe is written so, so well. Zero credit to me; all credit to Claire. It makes exactly 42 cookies every time, without fail. Claire’s cookbook is so well-written for that reason, and a great one to make you fall in love with baking. They also can be frozen, so I always make them first! Also, everyone raved about these last year, and my dad evaded a speeding ticket by giving his molasses cookies away to a cop.

Sadly, these were the cookies that made me realize my oven was broken. Most came out okay the first round, but some burnt and others didn’t have a beautiful crinkle top so I actually baked this recipe twice. The second time I watched my oven like a hawk and bought new baking soda because I realized mine was a little old. Crinkled perfection! (I couldn’t give a mediocre cookie to my new neighbors!)

Andes Mint Cookies

From Maria Lichty

I’ve made Andes mint cookies with my mom for Christmas since I can remember. They’re actually really basic—just a chocolate cookie with an Andes mint on top—but they look so festive with how the Andes mint swirls the white and brown. This isn’t the recipe we used growing up, but still is great.

However, I also botched this recipe because I wasn’t paying attention and added less cocoa powder than called for. Then when I added the remaining powder later, it didn’t mix well and I still was burning cookies…so I also made these twice too.

Soft Almond Sugar Cookies That Are Very Thick and Glazed and Fun

From Molly Yeh

I first started making these for Valentine’s a few years ago and I refuse to make any other sugar cookie! The almond flour, Princess Emulsion, and lemon zest make it so special, and they are thick and soft and melt in your mouth. I had my oven under control by the time I made these, so they baked well enough. Some browned more than I wanted, but I made about 75+ by doubling the recipe, so I was covered for mistakes.

These did teach me a lesson in patience, though. My first go at icing these with a glaze I decided to skip the thicker outline consistency and just wing it. Bad, bad, bad. They were so ugly! My reputation as a new neighbor was at stake. I had a crisis that I was the worst cookie decorator on the planet, took a night off, and regrouped. The next day I did nothing but glaze these, making a thicker consistency glaze then swapping it to a fill glaze. Much, much prettier. Glaze is much harder to do fun designs with, but I prefer the flavor to Royal icing! My aunt is a pro decorator with Royal icing, so I knew her cookies would represent well in the looks department on Christmas Eve whereas mine…were so-so.

Triple Chocolate Peppermint Bark

Baking for the Holidays by Sarah Kieffer

This is a new recipe I tried this year and HOLY MOLY it was so good. It was fairly simple, so giftable, and Diego and I went through our portion in less than 12 hours. My only mistake is that I made one batch. Next year I need to make a batch for Diego and me, and one for everyone else.

Iced Oatmeal Cookies

Midwest Made: Big, Bold Baking from the Heartland by Shauna Sever

I had Diego pick out the last cookie on the list, and he chose this one after I showed him A Cozy Kitchen making it. My parents/extended family are all from the midwest, and I think this brought back nostalgia for the similar packaged one. (I’ve never had it.) The dough is interesting because you make it in a food processor. It’s a super crumbly dough, so not very beginner friendly in my opinion. But it was a hit and went super well with coffee. Also decorating it was really easy!

How to have a personal British bake-off

Every recipe writer, Mary Berry, and chef will tell you—read the recipe twice. Guess what. I usually don’t do this and suffer. But not with a personal cookie bake off! In this case, I do a lot of reading before I get started. Here’s what I do:

Collect the recipes I want to bake. Usually this is about five, but can be more or less.

As the Christmas season approaches, I do this several weeks in advance and sometimes make a longer list of what looks good, then cut that list down. Basically, the cooks are on my mind for several weeks before I even start and I envision my perfect cookie box.

Read through each recipe, and take notes on what can be chilled or frozen. These are the recipes you should make first.
Create a list of all the ingredients needed. This is going to be a lot of the same stuff, but I try to keep a tally specifically on butter and buy a little more than needed. I also make sure to stock up on flour and sugar as well, even if I have a ton, because I don’t want to do #math and I hate a last minute grocery trip to buy one forgotten item more than anything!!
Create a schedule for either a full weekend or two weekends to bake. Take notes on chill times, bake times, etc. Do anything that can be rolled and frozen, or partially prepared first. If you’re new, only prep and bake 2–3 cookie types in a day.

Tip: Dedicate a full afternoon or evening to icing cookies if you are doing those. If you try to do it the same day you’ll have cookie fatigue and your decorations will be so ugly, re: my sugar cookies.

Get baking and take things slow! Unless you’re a pro or you have downtime while dough chills, try not to multitask.
Let cookies fully cool before stacking. As they chill, use a half sheet pan or cutting board to stack and store them, then eventually divide them for delivery!

Tips for packing cookie boxes

Whenever food bloggers or influencers post their Christmas cookie boxes pre-shipment, they look so cute. But if I’m honest, this styling drives me nuts. Even if you’re dropping a box off to a friend, if you don’t individually wrap each type of cookie all the flavors will start to mingle and suddenly your ginger cookies will taste like mint cookies. This happens too if you store a bunch of different cookies together. Don’t do it! Save it for the gram or for the holiday cookie plate where they’ll only be hanging together for a few hours before they are scarfed down.

Whether you’re shipping or hand delivering, here’s what I suggest:

Pick cookies that pack well! I already said that but if you want them to look nice, this is important. But if they do break they’ll still taste great.
Stack three of the same cookies together, then wrap them in saran wrap once or twice. Do this as many times as you need for each type of cookie. Then, put the cookies into a cute baggy. Repeat this with all the other cookies. (It seems like overkill but I swear it keeps them fresh and simultaneously looking cute/not breaking!)
Buy a metal tin or paper cookie box and store all the cookies inside this box. If you are extra nervous like me and shipping them, you can put them in a gallon bag inside the box. Shipping delays will not interfere with our cooks’ flavor and freshness!
Write a short note with a list of all the cookie names and include any nuts or other allergens. (Almond flour is a sneaky one here so don’t forget!) I wish more people did this, because often you get a cookie box and have no idea what you’re eating!
Ship! Or hand deliver. If shipping, try to do this early in December (and early in the week) otherwise it costs a pretty penny. If you can, aim for three- to four-day shipping and try to ship on a Monday. However, because you packed these so well they will be totally fine even after a week!

My oven saga

If you care, here it is. I want my woes heard!

Like I mentioned in the intro, my oven brought many baking complications. I’m by no means an expert, but I’ve baked for several years now, and some of the cookies I’ve baked I have perfected, meaning I know when something is my fault vs. the oven or other tools.

When we first moved into our house, I was sad about our smaller oven and skeptical if it was any good or that it would fit my half sheet pans (it does). Early on I would “slow-roast” a full chicken that was supposed to take hours and would be done in half the time. I wrote it off as just being a smaller oven, recalibrated it, then went about always cooking my food at the lowest time listed.

However when I began to bake, a lot of my cookies were burning black, especially in later batches. I am not that bad, so I knew something was wrong. A few weeks later I made sweet potatoes and they burned my hand through the glove. I immediately ordered an oven thermometer, and confirmed my oven was overheating 25–75 degrees higher!

We brought in a technician who tried to tell me things like “the oven is supposed to overheat by 75 degrees because when you open it it releases heat” and that all was operating as normal. I still asked for a new part, but he wouldn’t be back till Christmas Eve Eve, so I got to work baking anyway. Basically I would watch the heck out of my oven thermometer, then open the oven door to release heat when it overheated. It was a huge hassle, and had I not baked a lot before I probably would have given up. When our technician came back, our entire kitchen was filled with cookies, so I’m sure he thought I was nuts and a total liar.

But—after that the oven stopped overheating, and so I was right! Ha! He also didn’t accept any of my cookies.

What I bought and recommend

A kitchen scale

If you are buying anything, just buy this. Seriously! If you’ve ever baked cookies or anything and it comes out different each time and you don’t have a scale, this is why. Flour in particular can really vary when you scoop it. If two people were to scoop a cup of flour the weight can vary by a lot. A kitchen scale ensures you add the exact amount of your ingredients every time. I suspect anyone who thinks they are bad at baking just doesn’t have a scale, to be honest. Plus you can be so much lazier with a scale! Instead of getting out a bunch of measuring cups, you just dump everything into the bowl and weigh it as you go, so there’s less to clean!

An oven thermometer

I have no idea what took me this long, but I HIGHLY insist you get one. They are cheap and can teach you so much about your oven. Because of this, I was able to validate that my oven was overheating by 50+ degrees, even when a technician disagreed with me because he wasn’t obviously sitting by the oven for hours. Now that I had my oven fixed, it remains at the exact temperature and I can confirm that with this little guy!

Americolor food coloring

This is the best food coloring, but sadly you can’t go out and just buy it. It is really accurate to the color on the bottle, which is very helpful when adding color to your frosting. In a pinch I bought a different brand of what should have been a brick red food coloring from Hobby Lobby, but the color came out more like a maroon! If you can, try to buy at least a few Americolor basics, but if you are doing other brands I would test it out before adding to frosting. I had to add a lot of black Americolor to fix my maroon frosting as a result.

Great Jones half sheet pans

I have four half sheet pans, three of which are from Great Jones, and I still don’t think that’s enough when I’m baking a million cookies. They aren’t just great for baking, but are great for storage, for stacking baked cookies, and all sorts of prep. Plus, I love how colorful these are and they really retain their heat!

(P.S. A half sheet pan is what you’d probably call a regular sheet pan. Quarter sheet pans are smaller and underrated in my opinion! I love them. You definitely don’t have a full sheet pan in your kitchen. Trust me, it’s probably too big for your oven.)

Kitchenaid stand mixer

This goes without saying, but even if you bake a few times a year I think this is worth owning. I one time visited a friend’s house and suggested we make cookies. We got everything ready, and when there was no stand mixer I about gave up. I can’t even remember if the cookies were good because I am still traumatized by the labor of hand-mixing cookie dough. Your arm will thank you and you’ll be able to cream your butter and sugar to perfection.

They also are basically heirlooms. I’m using the one that my parents got as a wedding gift…over thirty years ago!

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What I baked for Christmas