Three men walk into a holiday party...
Hey Jon, Michael, Nicholas – thank you for writing in. Since all three of you basically asked the same thing, it's safe to say y'all are not alone in wondering what to wear this time of year. The holiday event waters are cheerful (slice up the fruitcake…) but can be confusing to navigate. I mean, a holiday open house at your neighbors' has a different vibe than, say, a year-end party with the managing partners at your firm. But my advice on holiday dressing is pretty straightforward and I hope applicable to everyone, no matter your level of festivity.
And that is: pick just one thing that feels right... and then don't be afraid to keep wearing it. (We're big proponents of repeating an outfit, no matter what time of year.) In this case, it's basically what you'd wear to a party any other time of year – sport coat, dress shirt, 5-pockets or trousers – but with one element swapped out for its "holiday" equivalent.
For example. If you're someone that really likes to get dressed (let's call this level 3) and you don't mind being the lead singer in the room – go bold. A sport coat in tartan or bright red corduroy is a good way to get in some holiday cheer that's visible from across the room. Just make sure the rest of the look is discreet: 5-pockets or charcoal trousers, solid shirt or sweater. Maybe even a turtleneck. Pants are another sneaky-good way to make a statement. This pair in red and green wool tartan is begging for a holiday party invite. Again, fantastic, but not for the faint of heart. Wear with a quiet, solid sweater or a navy blazer and go on with your bad self.
If party pants are too much of a statement for you, maybe you're more of a Level 2 guy. I tend to fall into this category. You're looking for something that looks festive, but not necessarily from a distance, which is more likely to be something you can wear throughout the whole season, not just for holiday parties. Y'all know how I feel about green sport jackets and the spruce leno is as versatile as they come. It makes you look like the guy who dressed up for the holiday dinner, but you'll look just as appropriate wearing it out to cocktails at virtually any other time of year. (And if you're curious about green jacket life, whether you've got an upcoming event or not, now is the time. We're no longer able to produce the fabric, so until we find a new maker, this is the last of the leno-weave. Get in there.) The same idea can be achieved with a more subtle use of color – a sweater in rose or forest or pine. Maybe purple if you're an Advent guy. I've also worn green cords for Christmas... these emerald ones have a nice brightness to them.
Lastly, more conservative dressers fall into Level 1, where you want to look quietly festive. For you, I'd say a navy blazer with a small pop of interest somewhere else. A pocket square with a little red or green in it... a tartan or Christmas tree bowtie... a solid red knit or foulard tie. Just a small, wink-and-nod element. The spiritual opposite of a 'tacky holiday sweater'. On the more utilitarian side of things, even a plaid wool scarf will give off a festive vibe before you even walk in.
Anyway, don't stress too much here... and remember you don't need a ton of 'holiday' outfits. Just put a little effort into your look as you would at any other time of year, pick your one thing, and wear it proudly all season. Even if that one thing is a Santa Suit. There's room for that, too.