Christmas is not the time to play it safe. Ugly sweaters, loud prints, questionable amounts of red and green; holiday dressing is one of the few times of year when wearing something ridiculous is practically encouraged.
Whether you're looking for an ugly Christmas sweater for the office party, a festive shirt for Christmas dinner, or something that'll get a laugh before you've even said hello, there's plenty of room to have fun with what you wear.
And that applies regardless of your size. From Regular to Big & Tall, finding the right fit shouldn't mean compromising on the styles you actually want to wear.
Here's how to choose your Christmas outfit, find the right fit, and make the most of the festive season.
Christmas Clothing Should Actually Be Fun
There are plenty of occasions when a simple shirt or a plain sweater makes sense, but Christmas gives you an excuse to try something with a little more personality.
Maybe it's a sweater featuring Santa pole dancing, a shirt featuring an outrageous Christmas graphic, or a print that makes people look twice. The best festive outfits tend to be the ones that get a reaction, whether that's a compliment, a laugh, or someone asking where on earth you found it.
Of course, not everyone wants to turn up looking like a walking Christmas decoration. Some prefer a more understated festive pattern, while others are perfectly happy to wear the loudest thing in the room.
Neither approach is wrong. The point is to choose something you enjoy wearing rather than worrying too much about whether it's considered fashionable.
Christmas Sweater or Christmas Shirt?
Both are great options for getting into the Christmas spirit, but the better choice usually comes down to the occasion, the weather, and how you prefer to dress.
Ugly Christmas Sweaters for Men
An ugly Christmas sweater is difficult to beat for office parties, ugly sweater competitions, holiday drinks, and any event where subtlety isn't really the goal.
The appeal is pretty straightforward. You get to wear something deliberately ridiculous, and everyone else is encouraged to do the same. Whether you prefer classic Christmas graphics, terrible festive jokes, or something a little more unexpected, there's no shortage of ways to make an impression.
Sweaters are also practical when the weather turns cold, especially if you want an outfit that doesn't require much thought. Pair one with jeans or chinos and casual shoes, and you're ready to go.
If you're shopping for a particular event, it's worth checking whether the invitation specifically calls for an ugly Christmas sweater. A festive shirt might look great, but it may not quite meet the brief if there's a sweater competition involved.
Christmas Shirts for Men
Christmas shirts offer a little more flexibility, particularly if you're attending several different events throughout the season.
A festive button-down works well for Christmas dinner, family gatherings, work parties, and casual holiday drinks. Depending on the print, it can look relatively polished or every bit as ridiculous as an ugly Christmas sweater.
They're also a good alternative if you live somewhere warmer, tend to run hot, or simply don't want to spend an entire evening inside a chunky sweater.
Wear yours buttoned up with chinos or trousers for a more put-together look, or leave it open over a plain T-shirt for something casual. You can also add a jacket when heading outside without having to completely rethink the outfit.
And if the print happens to involve Santa doing something he probably shouldn't be doing? Even better.
What to Wear to an Ugly Christmas Sweater Party
If the invitation specifically says ugly Christmas sweater party, you have permission to commit to the theme.
A classic Christmas pattern will certainly do the job, but if you're hoping to win an ugly sweater competition, you might want to look for something a little more memorable. Bold graphics, ridiculous illustrations, and festive jokes are all fair game, particularly when everyone else is competing for the same attention.
The easiest way to style an ugly Christmas sweater is to let it be the main event. Dark jeans or chinos work with almost any Christmas design, while casual leather shoes or clean sneakers keep the outfit comfortable for an evening of socializing.
For a work Christmas party, you can make the outfit slightly more polished with straight-leg trousers and simple shoes. If it's a casual gathering with friends, jeans are perfectly fine, especially when the sweater is already doing most of the talking.
Of course, if your goal is to win the office competition rather than demonstrate impeccable taste, we'd argue that normal fashion rules have temporarily been suspended.
How to Style Christmas Shirts and Sweaters
When your Christmas shirt or sweater already has a bold print, the rest of your outfit can be relatively simple. A few well-chosen basics will let the festive design stand out without making the whole outfit feel too busy.
For Christmas dinner or family gatherings, a festive button-down with straight-leg trousers or chinos offers a slightly more polished option. Choose a darker print for something understated, or go all in with a colorful Christmas design if your family appreciates a good joke.
For casual holiday drinks, try wearing a Christmas shirt open over a plain T-shirt with jeans and sneakers. It's an easy way to wear a louder print without committing to a fully buttoned-up look, and it gives you the flexibility to add or remove layers depending on the temperature.
For office Christmas parties, either option can work depending on the dress code. A festive shirt with dark trousers is a good choice when the occasion calls for something smart casual, while an ugly Christmas sweater is ideal if the event has a more relaxed atmosphere.
You can also make your Christmas outfit feel more intentional by picking up one of the colors from the print. A sweater with navy details, for example, will pair naturally with navy or dark denim trousers, while warmer Christmas colors often work well with neutral shades such as black, charcoal, or khaki.
The main thing is to choose an outfit that feels comfortable and suits the occasion. You don't need to overthink it, particularly when the whole point of festive dressing is to have a little fun.
Finding the Right Fit: Regular, Big & Tall Christmas Clothing
The Christmas design can be ridiculous. The fit doesn't have to be.
Whether you're shopping for an XL or need an extended size, finding a Christmas sweater that fits shouldn't mean compromising on style. At Eleven Oasis, our ugly Christmas sweaters are available in sizes up to 6XL, so there's more room to find something festive that fits comfortably. Always check the individual product's measurements and available sizes before ordering.
For sweaters, pay particular attention to the chest, body length, and sleeves. A sweater that's too short may ride up when you move, while one that's unnecessarily wide can feel bulky, especially when layered over another shirt.
For Christmas button-downs, check the shoulder fit and chest measurements, along with the overall shirt length. If you prefer wearing your shirt untucked, make sure it falls at a comfortable point rather than sitting too high on your waist.
When Should You Choose Big or Tall Sizing?
One of the most common mistakes when shopping for men's clothing is assuming that going up a size will solve every fit problem.
If your usual size fits comfortably through the chest and waist but the sleeves or body are too short, you may benefit from a Tall size rather than simply choosing a wider regular fit.
For example, an XL and XLT aren't necessarily interchangeable. The T generally indicates additional length, although the exact measurements depend on the product.
Similarly, if you need more room through the chest or waist without additional length, choosing a larger regular size or an appropriate Big fit may be more suitable.
Whether you're looking for a 3XL, 4XL, or 5XL Christmas sweater, or need additional length in a Tall size, it's important to compare the individual product measurements rather than relying on the size label alone.
At Eleven Oasis, selected styles are available in Regular and Big & Tall options, although the available sizes and lengths vary by product. Check each product's size information before ordering to make sure you're choosing the right fit.
If you're unsure which sizing category suits you, our Big vs. Tall vs. Big & Tall: Which Fit Do You Need? guide explains the differences and how to take your measurements.
Shop Christmas Sweaters and Shirts at Eleven Oasis
Christmas is one of the few times of year when wearing something completely over the top is actively encouraged.
Whether your idea of festive dressing is an unapologetically ugly Christmas sweater, a loud holiday shirt, or something you fully intend to wear long after December, there's no reason to settle for something boring.
At Eleven Oasis, our Christmas collection brings together festive graphics, playful designs, and plenty of personality. With ugly Christmas sweaters available in sizes up to 6XL, there's no reason your size should limit your holiday style.
Find something that makes you smile, gets a laugh, or gives you a legitimate shot at winning the office ugly sweater competition.
Frequently Asked Questions
What should men wear to an ugly Christmas sweater party?
An ugly Christmas sweater paired with jeans or chinos and casual shoes is a straightforward choice. Look for a bold festive graphic, funny design, or deliberately over-the-top pattern if you want to embrace the theme. If there's a competition involved, a more unusual sweater might help you stand out.
Can you wear a Christmas shirt instead of an ugly Christmas sweater?
Absolutely, provided the event doesn't specifically require a sweater. Christmas shirts are a great alternative for holiday dinners, casual gatherings, and warmer venues. They can also be styled with chinos or trousers for a slightly more polished festive outfit.
How should a Christmas sweater fit?
A Christmas sweater should feel comfortable through the chest and waist, with enough room to move and layer without being excessively loose. Check the sleeve and body lengths, particularly if regular sizes tend to run short on you. Always compare the individual product measurements before choosing your size.
Is XL the same as XLT?
No. An XL and XLT generally have different proportions. XLT is a Tall size, typically designed to provide additional body and sleeve length compared with a regular XL. The exact measurements vary by product, so check the size chart rather than assuming the two sizes are interchangeable.
What sizes do Eleven Oasis ugly Christmas sweaters come in?
Eleven Oasis ugly Christmas sweaters are available in sizes up to 6XL, giving shoppers more options beyond standard sizing. Availability may vary by design, so check the individual product page for current sizes and measurements.
