Holiday Attire for Men: What It Means & How to Wear It

The holiday attire dress code can be confusing, as it can mean anything from cocktail attire with a festive twist to the recent vogue for ugly Christmas sweaters. No matter whether it’s for an office Christmas party, New Year’s Eve, or just to spread some holiday cheer, this is the only guide you’ll need to infuse some sophistication into your festive outfits.

Holiday Attire: The Golden Rule

Thinking Formal is Never Going to Offend

Our most general piece of advice for the holiday or festive dress code is to gravitate to the more formal end of the spectrum which we’re going to lay out today. After all, no one is ever going to fault you for looking put together. The exception to this advice, of course, is if the hosts have clearly stated that the party is going to be more extravagant and playful in nature and that an ugly Christmas sweater is expected. In that case, by all means, do loosen up and have some fun.

Your safest bet, of course, will always be to ask the hosts for advice directly as a gentleman always makes the effort to follow a dress code as closely as he can; to do otherwise would be an insult to your hosts. One more piece of general advice here before we dive in, keep it varied and have a few options handy, after all, it’s a busy time of year for parties and you may be invited to more than one that has a holiday or festive dress code to it so having a few options at your disposal will never be a bad thing.

The Holiday Attire Video Guide

Some say that singing loud is the best way to spread Christmas cheer – while we’re happy to join in a carol or two, chances are you’re also just as comfortable by the fire with your favorite holiday cocktail, gaining some inspiration for your festive ensembles with a video guide. Cheers!

How To Meet The Holiday Attire Dress Code Stylishly?

The simplest answer is this, think of it as being an offshoot of cocktail attire with an extra holiday touch in terms of color or some playfulness that’s incorporated into your outfit such as wearing tartan which has been an established alternative when it comes to holiday wear since at least the middle of the 20th century. Regarding color then, do feel free to incorporate some of the standard colors of the holiday season such as red and green. With that said, however, don’t go for bright and gaudy hues as these are just going to make you stand out a little bit too much. Instead, go for something subtle, understated, and elegant.

Now let’s cover today’s subject through the lens of multiple different types of holiday parties, each with differing levels of formality, and cover the related dress accordingly.

Office-Appropriate Festive Attire

Regarding how dressed up you should be for such an event, just take a cue from the regular day-to-day attire at your office. In other words, think of how you should dress as being a somewhat typical office outfit, maybe just a bit more relaxed and with a seasonal element to it.

White Collar Office Parties

Firstly, if you work in a traditional white-collar office environment, go for something that’s appropriately conservative. For example, a suit perhaps three pieces or double-breasted in a dark color like charcoal, navy, or in midnight blue, if you’re feeling especially elegant. Along with this, you could go for a dress shirt, ideally French cuffed and probably in a pastel color as white might be just a bit too stuffy for a festive party.

In terms of shoes, you’ll want to keep things appropriately conservative as well so you could go for the classic black cap toe oxford or if you’re feeling just a little bit more playful, something in a very dark brown color perhaps an oxblood. You could go for something like a monk strap or something incorporating just a little bit of broguing in its design but you don’t want to get too crazy and you probably won’t want to opt for light colors like tan either. After all, if your regular office attire consists of those black oxfords, you’ll want to keep it in the neighborhood of that kind of shoe even for a party like this.

As for your accessories, the novelty tie emblazoned with huge Santa heads is probably going to be a little bit too informal for a party of this nature. Instead, you’ll want to go for something like a dark burgundy or a similarly muted hue perhaps with a slight pattern to it. Although solids are of course a safe bet. Your pocket square can be a little bit bolder in comparison to your tie and can possibly incorporate some small patterns as well. Just remember that all of the elements of your outfit should ultimately remain harmonious.

You’re likely going to have the most latitude here with your cufflinks, they can be solid metal in any shade of course and can incorporate stones or other engraved designs. This type of party is just playful enough, however, that you could also do something with miniatures, say, for example, a tiny reindeer just so long as it’s understated and subtle. Have fun with it and try to strike that ideal balance between formal and festive.

Tie bars, collar clips, and rings can also be worn as long as they are similarly understated and of course, matching your metals is always a good idea. Finally here regarding boutonnieres, something light-colored and small so as also to be understated would be an ideal choice.

Less Formal Office Parties

For a slightly less formal type of office party, we recommend that you go with a combination of sport coat and odd trousers. A patterned or textured sportcoat would be a good choice here with or without a tie. Something for example in herringbone, houndstooth, or a mottled tweed will provide a rustic quality that’s still appropriate for the season. Wearing a blazer with a tartan or other plaid pattern would be an ideal way to be seasonally appropriate, a little bit bold, and a little bit rustic all at the same time.

Finally, this would also be a great opportunity to break out something like a burgundy velvet jacket if you’re feeling especially avant-garde. Your shirt could be plain in color, either in a pastel shade or alternatively in a rich dark hue if you’re going for something a little bit more fashion-forward. Also, the shirt could feature a pattern just so long as that pattern doesn’t clash if you’ve also got one in your jacket.

In terms of styling and materials, choices like the Oxford cloth button down or OCBD would be appropriately semi-formal. A chambray shirt would be another good choice or alternatively, you could substitute the collared shirt altogether for something like a dark turtleneck sweater under your jacket. You can round out this look with some flannel trousers or corduroys. As far as shoes are concerned, you could opt for something like wingtips or loafers just so long as they’re well shined.

Casual Office Parties

Our advice is largely the same as for semi-formal office parties but with a few key distinctions.

First of all, you can feel free to swap out the sport coat with a cable knit pullover or a cardigan sweater in a warm color. Alternatively, a fair isle sweater or sweater vest will allow you to stand out a little bit more while still looking rustic and traditional.

In addition to flannel trousers and corduroys, a casual office party would also be an appropriate time to break out dark denim or perhaps even colored chinos if you’re feeling especially bold.

Finally, you can add an accent with some brightly colored dress socks or maybe incorporate your crazy socks featuring Santa and his reindeer here and you can round out the look with some informal shoes or perhaps a dress boot.

Should You Wear (Ugly) Christmas Sweaters?

Certainly not for everyone, but also seemingly difficult to escape from during the festive period, the ugly Christmas sweater is often pictured as de rigueur for many holiday events. Watch our video on the topic to help decide whether you should (or shouldn’t!) add one to your closet this Christmas.

Residential /Private Holiday Parties

Now let’s briefly cover some advice on what to wear to a holiday or festive party given in a residential or otherwise similarly private setting.

In the broad strokes, you’re going to want to keep things a little bit more relaxed for a home party than you would for an office party but the breakdown we’ve just given for three different formality levels of office parties can still hold mostly true here as well.

In other words, all of the suggestions we gave for specific combinations of garments still hold true for home parties as they did for office parties but when we gave you more than one option in some of our breakdowns, you would here opt for some of the less formal of those options.

For example, at a semi-formal or mid-level holiday house party, you could perhaps go for the turtleneck sweater before going for the button-down. Remember, the bottom line for house parties is always the dress code that’s printed on the invitation and/or the personal advice of the hosts. If the party takes place during the holiday season but the invitation says black-tie, wear a tuxedo and leave that tweed sport coat at home.

Conclusion: Holiday Attire Doesn’t Have to Be Confusing!

While the holiday or festive dress code covers a wide range of levels of formality, it doesn’t have to be a source of anxiety. For a party at work, take a cue from your regular office attire and add a twist or two and for a residential party, take your cue from the invitation and the advice of the hosts and feel free to be just a little bit more relaxed and playful and yes, if ugly sweaters are expected, do loosen up and feel free to have a little bit of fun.

Outfit Rundown

It consists of a muted brown cardigan sweater for a seasonal touch over a shirt in a light cream yellow that features a broken check pattern of green purple pink and burnt orange. The olive green knit tie provides more texture and a more seasonal color. My corduroys which are in a warm almost mustardy brown color are similarly casual and my socks echo my shirt. In that, they’re also sort of a cream yellow color but they feature an argyle pattern in white and light blue.

I’m rounding out the outfit today with some medium brown wingtip derby shoes that feature heavy broguing. As you might be able to tell, I’m not really wearing very many other accessories today. My shirt even has barrel cuffs so I’m not wearing any cufflinks. I just figured this would be a good example of a very casual outfit that still fits the holiday mold and I’m sure you’ve seen several other examples of more formal outfits throughout the video.

What sorts of combinations have you worn to holiday parties in the past? Share with us in the comments section below.