The Ultimate Guide to Feeling Beautiful While Winning an Ugly Christmas Sweater Contest

Get ready, party people! It is Christmas time and I need an ugly Christmas sweater. We created an ugly Christmas sweater guide. This guide will give you the competitive edge to the next contest.
First, we’ll prep you with the history of the beloved Christmastime competition. Then, we’ll equip you with all the deets on how to win the contest at every last bash of the season as you sleigh your way to the new year.
This year, don’t just settle for your holiday bonus. Hello, there are prizes at stake! And trust us, Santa will know if you think you’re “too cool” to get in on the fun. Then, it’s straight to the naughty list for you.
The Ugly Christmas Sweater: A History
The origin of the ugly sweater competition is cloaked in mystery. (Pun intended.) While no one can pinpoint their exact emergence onto the scene, the frump-tastic, seasonal favorites have amassed cult-followings year-round. With these holiday-savvy styles, literally anything goes. The more decked-out your garb, the better. Whether you’re “Single and Ready to Jingle,” have a passion for cats, or you’re always down to get punny, nothing should hold you back from getting lit in a hideous cardigan this December.
Getting Started: What You’ll Need
The bottom line is that homemade versions are natural winners. Why? Because you just can’t beat the originality of a made-from-scratch design. We won’t judge you for grabbing a mass-produced pullover, but it’ll be no match for a cleverly crafted DIY-er.
Here are a few essentials to consider as you begin your journey towards holiday streetstyle stardom:
- A Sweater or Sweatshirt (Duh)
- A Theme (A Jack Skellington or Mr. Hanky patch, perhaps?)
- Photo transfer emulsion for personalized holiday wear
- Red and Green Pom Poms
- Festive Buttons. The tackier the better!
- Patches and Iron-Ons
- Bells, Lace, Ribbons and Craft Supplies.
- Iron-On Letters, Stencils and Puffy Fabric Paint.
- A Hot glue gun or sewing kit
- Scissors
DIY the “Artfully Ugly” Sweater of Your Dreams
Decorating your new winter woolen is the fun part, but patience is key. Start by brainstorming to come up with a theme or aesthetic for your project. For instance, Disney loyalists should appreciate a Santa Claus Mickey design. But mixing-and-matching with a decal from The Nightmare Before Christmas won’t go over well with the judges.
If your inspiration has run dry, it helps to choose a tone. Are you feeling sentimental, sassy, or just plain punny this year? Deciding on the mood that you’re going for can be what it takes to get your creativity flowing.
Next, set up your crafting station with the various tools you’ll need. Depending on your selected materials, you might need a hot glue gun, a sewing kit, scissors and more.
Finally, take your time before making things permanent. Try out different designs to see which one calls to you before attaching your holiday swag. A well-thought out aesthetic is what upgrades a tacky sweater design to “artfully ugly” territory.
Here are some YouTube tutorials to help you craft your way to ugly sweater perfection:
If You’re Feeling Lazy…
Like we said, we won’t judge you for picking one up at the store. In fact, many designers launch holiday-themed merch for the fashion-savvy consumer.
Want some help picking out the ultimate ugly sweater? Check out our Top 5 Beautifully Ugly Christmas Sweaters to Rock this Holiday Season
Before you click “add to cart,” these are shoppable styles in trending themes for holiday wear this season. Hint: We’re all about the unexpected “ugly” sweater dress this year. Ugly Christmas Sweater guide to buying below.
- Game of Thrones-Satire
- Mean Girls “Glen Coco” Shout-Out
- Cat-Tastic Crew Neck
- Men’s Playful Reindeer Poop Pullover
- Men’s Antler-ed Hoodie
- TMNT Throwback
- Home Alone Themed Knit
- Women’s Sparkling Lights Sweater Dress
- Boozy Puns
- Irreverent Adult Knitwear
- Cannabis-Themed
- Poking Fun at Politics
In Conclusion
Ultimately, the key to feeling beautiful while wearing your ugliest sweater ever is knowing true beauty is on the inside. Nothing you wear this holiday season can take that away from you. (Except polyester.)

Are you making a DIY Ugly Christmas sweater this year? We want to hear about it in the comments below!