Finding practical christmas holiday outfit ideas requires matching your clothes to your specific event schedule. A formal dinner with your boss requires different clothes than a neighborhood potluck. You need solid options that work for your exact plans and climate.
We organized ten items from our Christmas Apparel collection to wear this December. Every item we sell is printed to order. This means you have the flexibility to coordinate a large group of relatives or just pick one specific design for yourself. Plan this today. Figuring out what to wear early gives you time to focus on buying gifts and planning meals. Let us look at some practical ways to sort out your December clothing.
Warm Weather Holiday Christmas Outfit Ideas
If you live in a warmer climate or plan to spend December on a beach, heavy sweaters will make you miserable. A button-down shirt offers enough formality for a nice dinner reservation while keeping you comfortable indoors. These options work well for coordinating large family groups across multiple generations. You can easily pair these with jeans or khakis for a clean look in your group photos. Review our advice on 10 Outfit Ideas for Christmas Party Gatherings if you need to coordinate with coworkers in a warm office.
Hawaiian Shirt – Christmas Snowmen
A busy all-over print shows happy snowmen wearing top hats and red scarves. They are surrounded by detailed red poinsettias and green winter foliage against a black background. The short sleeves make it practical for indoor gatherings where the heating is turned up high. If you want to use this for a family portrait, position your group in front of a solid light-colored wall so the dark background of the shirt stands out clearly.
Shop now $19.99
Matching Family Hawaiian Shirts – Surfing Santa Christmas
The green background is covered in illustrations of Santa catching waves on a yellow surfboard. He wears striped swim trunks and his classic red hat among tropical palm trees and red hibiscus flowers. Buying three or more items saves 10 percent on your entire order. This is a practical choice if you are renting a beach house for the week and want a matching look for your morning walks.
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Matching Family Hawaiian Shirts – Christmas Goose
This light green shirt features a large flock of cartoon white geese on the front and back. Several of the geese wear red Santa hats and green winter scarves. One goose even wears a pair of red holiday glasses. The pale green color photographs well outdoors in natural daylight. Check the size chart on the product page to verify you get the right fit for everyone in your group.
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Matching Family Hawaiian Shirt – Motorcycle Santa Desert – Christmas
A repeating all-over print shows Santa Claus riding a red motorcycle through a sandy desert landscape. He carries a green bag full of wrapped presents on the back of his bike. The scenery includes tall stone arches and green palm trees under a blue sky. You can wear this to a casual neighborhood barbecue. Match it with solid dark pants to let the busy print be the focal point.
Shop now $19.99Humorous Christmas Holiday Party Outfit Ideas
Casual gatherings with your friends or coworkers usually call for something funny. A novelty sweater design fits the standard dress code without making you feel out of place. Take a look at our Funny Christmas Apparel collection for more examples. When you pick a humorous design, keep the rest of your clothing simple. Solid colored pants and basic shoes keep the attention on the print. Read our guide on 10 Christmas Outfit Ideas for Women Attending December Events if you want more specific styling tips for casual events.
Ugly Sweater – Santa Riding Rooster – Black
This black sweater design displays Santa holding a golden bell while riding a giant rooster. The bird has bright orange and green tail feathers. The snowy background includes decorated pine trees and classic fair isle borders in red and green. The faux-knit pattern gives it the traditional holiday look. Have fun tonight. This works well for an evening trivia night at your local pub.
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Ugly Sweater – Christmas Alien UFO – No Personalization
A green alien wearing a Santa hat pops out of a flying saucer on this dark sweater print. The UFO is decorated with colorful string lights. Red candy canes and green presents float around the retro outer space pattern. This is a very busy design, so you should avoid wearing any patterned hats or scarves with it. Pair it with dark jeans for a simple party outfit.
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Funny Donkey Ugly Sweater
The front graphic centers on a screaming gray donkey wearing a red hat, framed by a green holly wreath. The word AAAH sits right above the donkey. The rest of the red background mimics a traditional knitted sweater with rows of white reindeer and green pine trees. You can wear this to an ugly sweater contest at your office. Remember to check the size chart to find your exact measurements before ordering.
Shop now $33.99Custom Holiday Christmas Party Outfit Ideas
Sometimes you need clothing that sits right between formal and casual. A customized jersey or a simple polo shirt fills that gap nicely. Personalized items allow you to put your name directly on the clothing. If you are organizing a large group photoshoot, review our tips in 10 Christmas Photos Outfit Ideas for Your Group. You can match the whole family in our Matching Family Pajamas or opt for individual jerseys so everyone has their own name printed on the back.
Christmas Baseball Jersey – Glitter Snowflake – Custom Name & Number
This blue baseball jersey features a dense white snowflake pattern near the hem that fades toward the shoulders. The texture looks like blue glitter printed flat onto the item. You can add your own custom name and number directly on the product page before ordering. This is a practical choice for attending a winter sporting event or a casual family bowling night.
Shop now $23.99
Ugly Sweater – Santa & Christmas Tree
A large illustration of Santa Claus holding a brightly decorated Christmas tree takes up the front and back of this white sweatshirt design. A string of colorful bulbs wraps around the lower sleeves and waist. The white background makes the red and green colors pop clearly in photos. This works well for a casual family dinner or a morning spent wrapping presents in your living room.
Shop now $33.99
Polo Shirt – Christmas Horses
Small red and green galloping horses create a repeating pattern across this white polo shirt. Subtle green stars sit between the horses. You can wear this on the golf course or to a daytime lunch gathering with older relatives. The collar adds just enough formality for a country club dress code. Buying three or more items from our store saves you 10 percent on the total order.
Shop now $23.99Planning Your December Wardrobe Successfully
Waiting until the second week of December to figure out your clothing will cause unnecessary stress. Because our store prints every item to order, you need to allow time before your event. Order early so you have your items ready for your scheduled photos and parties. You do not want to be the only person in a family portrait missing a coordinated shirt.
Sizing requires a little extra attention when you buy for a large group of people. Do not assume a medium in a polo shirt fits exactly like a medium in a baseball jersey. Each product page has its own specific size chart. Measure a shirt you currently own and compare those exact numbers to the chart before adding anything to your cart. This is extremely important for matching groups with varying heights and builds. A teenager might need an adult small in one garment style and a medium in another. Taking five minutes to measure will save you from an ill-fitting shirt on the day of your party.
If you choose to customize a product, double-check your spelling. Personalized jerseys take a name and number exactly as you type them on the product page. A small typo can ruin an expensive family photo. Read the text backward to catch spelling errors before you hit the checkout button. Have a second person look at the screen to verify the numbers match what you intended.
Planning a photoshoot involves more than just picking the shirts. Think about your background and lighting. A busy printed shirt works best against a solid backdrop or a simple snowy field. If you are standing in front of a highly decorated tree, a simpler pattern might be easier to photograph without clashing. If you are taking photos indoors, try to face a window so the natural light hits the front of your shirts. Overhead indoor lighting can cast harsh shadows that obscure the printed designs.
- Order early for your planned events to allow for printing.
- Check the size chart on each individual product page.
- Measure a shirt you already own for comparison.
- Verify custom names and numbers carefully before checking out.
- Buy three or more items together to save 10 percent.
- Consider the photo background before choosing a very busy pattern.
Having a solid plan makes the busy weeks ahead much easier to manage. You can focus on enjoying your events instead of scrambling to find something appropriate to wear.
Frequently asked questions
Do I need to buy the same size for a jersey and a Hawaiian shirt?
You should always check the size chart on each specific product page. Our different garment types have different measurements. A large in one style might not match a large in another. Measuring a shirt you already own and comparing it to the chart is the best way to get the right fit.
Can I add my name to any of the shirts in your store?
Only specific personalized items allow you to add your name. If an item can be customized, you will see a text box for your name directly on the product page. For personalized jerseys, you will also see a box to add a custom number.
Is there a discount for buying matching shirts for my whole family?
Yes, there is a discount available for larger orders. When you buy three or more items from our store, you automatically save 10 percent on your order. This applies if you buy multiple copies of the same shirt or mix and match different designs.
How should I coordinate outfits for a large family photo?
You can either buy the exact same matching shirt for everyone, or pick a color theme. If you pick a theme, have everyone wear different shirts that share a dominant color like dark green or bright red. Have everyone wear the same style of pants to keep the photo looking organized.
What should I wear if I am attending an outdoor event in a cold climate?
Layering is a practical choice for cold outdoor events. You can wear one of our printed shirts over a long-sleeved thermal top, or layer a heavier jacket over a printed sweater. Just keep the printed design visible when you take your group photos.
Prepare Your Holiday Closet Now
Getting your clothing sorted out early gives you one less thing to worry about later in the month. Review the options that fit your upcoming plans and coordinate with your family members to keep everyone on the same page.
Browse our complete Christmas Apparel collection to find the exact styles you need for your next gathering.
