Life of the Party

There’s no need to play it safe when it comes to building a lasting holiday wardrobe. This season, get festive—one velvet slipper, tartan tie, and reindeeer sock at a time

It happens to the best of us.

One man—we’ll call him Nick—received an invite to a festive dinner, just two days before the event itself. Despite being a man of taste and style, he didn’t have anything proper to wear. He’d been warned that these friends took dressing very, very seriously, so he went to the nearest thrift shop and found a black dinner jacket that didn’t exactly fit, but didn’t exactly not fit, either. Being industrious and short on time, he set about tailoring it himself, with the goal of bringing it in 2 inches. And so, the day of the event, he found himself in his dimly lit apartment, steaming the jacket’s front (to open it up) and stitching the back (to make it fit). Miraculously, it worked—the only problem was that he hadn’t noticed he’d used brown thread on a black jacket. Oops, but nothing that a black marker couldn’t fix. With about an hour to go, he had a jacket that mostly fit, bearing a trail of ink that only the closest observer could discern.

That man, Nick Sullivan, is now the fashion director at Esquire, and he remembers the story with a laugh as “an abject lesson in being prepared.”

“It taught me two things,” he says now. “One, the most memorable thing, if you’re hanging out with other people, is whether they make you feel comfortable—if people make you feel uncomfortable, you never forget. And two: Never, ever go unprepared ever again.”

And yet, this is often a season of unpreparedness. Perhaps you know the feeling. You get an invite to a festive gathering, with a dress code that’s either crystal clear (black tie, perhaps) or … less so. (“Elegant festive”? “Creative holiday”? No dress code at all?) Then suddenly it’s the day of the party and you find yourself making sartorial compromises. You buy something you like, but don’t love. Or you buy something you love, but spend too much on it. Or perhaps you make a trip to a thrift store, and bust out the needle and thread.

Suffice it to say, there is a better way. One that doesn’t require performing miraculous acts of tailoring at the 11th hour, with or without a Sharpie. As Sullivan suggests, that alternative is to prepare.

Based on my own life experience, along with conversations I’ve had recently with a few notable men of style (not to mention referencing the ever-flowing fount of inspiration that is Mr. Lauren), I can offer a few additional suggestions. For one, don’t be swayed by the fact that a holiday party purchase is something you’ll wear just one or two months a year. Invest wisely, and it’ll be something you wear for one or two months a year—for decades to come. And every time you do bust out those tartan pants, dinner jacket, or slippers, it’ll be an occasion.

And, as with any other long-term relationship, making a commitment to festive attire—whether it’s tartan trousers or a velvet jacket—should be done seriously and with great care, leavened with the same good cheer that defines the season. You’re looking for that unexpected piece that will draw the right kind of attention in 2018 and 2028. A good rule of thumb: If it’s something you could wear every day, it isn’t festive enough.

Ralph and Ricky Lauren at a 7th on Sale Black-tie Gala Dinner in <br/>New York City
Ralph and Ricky Lauren at a 7th on Sale Black-tie Gala Dinner in
New York City

This is the time of the year when you want to make an impression, whether it’s on your colleagues at the company party or via the inevitable party photos on your social media platform of choice.

It’s hard to go wrong with a pair of irreverant velvet slippers
It’s hard to go wrong with a pair of irreverant velvet slippers

“The good news about today is that there’s a pretty wide latitude of what’s acceptable to wear at all occasions,” says Nick Wooster, the longtime design consultant, Instagram style god, and a man who knows how to balance traditional clothing with personal style. “That’s a terrible thing for people who are purists or care about those things. But you can get away with something today that you might not have gotten away 25 years ago.” In his own wardrobe, that includes anything from velvet slippers to a plaid kilt he’s had for nearly three decades, though he acknowledges that look isn’t for everybody. “I think it goes back to that adage that if you buy the best you can afford, or if you stick with the most classic, you’re probably never gonna be let down,” he says.

If you’re truly unsure of where to begin, start with those classics, which are by definition timeless. This time of year, that would include a pair of trousers in a convivial color such as red or a traditional tartan. Velvet is decidedly in play. (Indeed, my go-to is a velvet dinner jacket, which can go with more formal get-ups or with jeans, à la Mr. Lauren.) For a sweater party, a bit of novelty is encouraged, even if it’s ultimately traditional. “I would go old-school and get a Fair Isle,” says Sullivan. “Maybe that would be sort of cheating,” he adds after a moment.

Feeling conservative? Season your look with suitable accessories like reindeer socks or a tartan tie. Or consider the Polo Bear. I have a pair of dress socks on which the iconic bear is enjoying a martini, just like I’ve enjoyed while wearing said socks to many a holiday party. After all, if you’re still not sure what to wear to your next swinging shindig, you can rest assured that the Polo Bear always will.

Paul L. Underwood is the former executive editor of He is based in Austin, Texas, where he lives with his wife and two children.
  • Photo courtesy of Getty Images
  • Photo courtesy of Ralph Lauren Corporation