5 Things To Wear To The Office Holiday Party To Make Your Coworkers Roll Their Eyes

December 13, 2019

Jack Lemmon at the office party in The Apartment.

It’s prime holiday party time — a month or so of fireside cocktails with the neighbors, of sharing time and connecting with loved ones, and of office holiday parties, where you can never quite tell if you’re at work (you are, even if you’re not). Our general advice for dressing for a holiday party is to dress well and seasonably, but not necessarily on theme. Although we like our points of distinction and encourage individuality, even mild eccentricity, we try not to wear too many items that would be considered conversation starters.

When determining whether to buy or wear something that might be deemed festive, a decent if not universal rule of thumb is to ask yourself whether you would wear the thing before December 1 or after December 25. A vintage sportcoat in a subdued reds and greens? Sure. A Viyella shirt (Royal Stewart or Dress Gordon are festive tartans). Accessories — a pocket square or even a pair of fun socks — in holiday colors or snowman? Acceptable. I’m not big on Christmas ties but I see the point.

I don’t know exactly where the line is. But there’s a line. A line between a coworker saying, “Hey, nice jacket,” and “Oh, heeeeeeey, nice jacket!” There’s parallels with holiday decorating… Hanging Christmas lights is great. Putting up a Christmas tree — the kids love it. Turning your living room into the North Pole, covering your house with enough lights to require a separate generator, setting out a full-on holiday tablescape? Corny.

Listed below are five items that your coworkers will tell you they love, but then snicker about when you go to the bar.

  • Grateful Dead Christmas bear needlepoint belt ($175) — Nothing gets a holiday crowd dancing like turning off Phil Spector’s A Christmas Gift to You in favor of Europe ‘72.  You ever notice that Jerry sorta looks like Santa? I like needlepoint, to a point; but I prefer belts I can wear year round.
  • Vineyard Vines party blazer ($325) — A true party blazer doesn’t need to call itself a party blazer. If you want something “fun”/i.e., mixed panels or patchwork, look for something vintage or just a subtle tartan.
  • A formal accessory worn casually (e.g., waistcoat from Ben Silver, $325) — For some reason, not much goes with “novelty” like suspenders. And an odd vest (with no jacket) seems to strike the right Dickensian note that makes it seem like a good idea this time of year. Avoid the temptation to mix dress codes and wear tailoring/tailoring accessories only if it makes sense.
  • Pretty much any explicitly holiday-themed sweater (Brooks Brothers, $98) — Worn ironically or not. Intarsia? More like… no-more-see-uh. A plain or textured sweater in a warm tone is a better fit.
  • Anything that lights up. Woah, Dasher; rein it in.

My wife, Courtney, suggested I add green pants to this list, to which I replied that I have green pants and plan to wear them to our holiday party. She told me, “Maybe that’s why I find them annoying.”