What to wear to a work holiday party at your boss’s house

We asked a few weeks ago whether company parties took place this year, and a number of you commented that the holiday party at your boss’s house would be somewhat smaller this year. Which brings us to something we haven’t discussed in years: What are your top tips for what to wear to a work holiday party at your boss’ house?

This is obviously going to vary based on your career, company, location and relationship with your boss – but I think there are some things to consider across the board.

What should you consider before choosing your outfit for the work party at your boss’s house?

The shoes. When I’m going to a house party, I’m never quite sure if the host will ask us to remove our shoes – so I hate wearing an outfit that relies on the shoes at all. For example, think about the outfit you would put together if you planned to wear over the knee boots – and then remove the boots.

Sometimes, even with tights, I layer them with a pair of socks under the boots, which would feel just as weird to keep wearing the boot socks as it would to remove the socks with the shoes. If you’re wearing socks or stockings, think about how well-maintained they are and whether there’s anything about them that you might not want your boss or people at the party to see. (My “if you can read this, drink wine” socks probably wouldn’t cut it.)

Although you DO keep shoes on, I could see some stilettos being difficult to wear hanging on looser rugs – so if you’re prone to tripping, these might not be the shoes for you.

How casual or dressy. This is always difficult and I would probably go for a middle ground unless otherwise expressly instructed by a dress code. Pants and sweater in a holiday-like color: yes. Jeans and sequin-heavy top: maybe? (Ugly Christmas sweater: maybe!) Leather pants – know your office.

(Skirts and dresses come back to the shoe issue for me—I tend to think heels are an integral part of these outfits, but your mileage may vary.)

Temperature. This might be a “me” problem, but I hate being cold as much as I hate being hot – so I would dress in layers. Many homes get really hot if a lot of people are inside – but windows or doors may be open to compensate (or make the party more COVID-friendly) so it can make it uncomfortably cold. (Or everyone’s favorite: sweltering hot in some areas but freezing in others, depending on how the air moves in the house.)

Hair and makeup. I would probably go for a blowout or a fun updo for the occasion and pull out my party makeup looks. If I’m going to eat or drink, I usually try to focus on the eyes instead of the lips, but maybe that’s me.

Consider the lighting. One final note: yes, you can fall into some bad light. Hosts can have harsh overhead lighting on, which (at least for me) will make my makeup and outfit look different than they would in a room more artfully lit with lamps. (It can also make some fabrics more sheer or otherwise revealing in the form of panty pants or cellulite (don’t care about either).) If you haven’t been before, there’s really no way to know…

Here’s how you know what to wear to your boss’s holiday party

When we last discussed This I noticed some more issues to consider with guidelines – I’d say these still hold up:

  • Is it a week night? Wear straight-from-work attire, but perhaps switch it up with festive jewelry, a sparkly sweater or a velvet blazer.
  • Are support staff invited? Depending on the office dynamic (and whether you often feel too young/not taken seriously by support staff), you might want to keep things on the more business-oriented side.
  • Is there a plus? This is a general clue that the Powers That Be are willing to loosen up a bit and festive attire may be appropriate.
  • Are children invited? Stay away from anything too dressy.

As always, if the party has been held before, you can ask someone who has gone before.

(The comments on the original post are fascinating – both for how to think about dressing for a holiday party if you ARE plus-sizedas well as the clothes that feel a lot more formal than I can imagine (most) people wearing now, like sheath dresses and black suits.)

Readers, what are your thoughts? What are you wearing – and what are your best tips for others on what to wear to a work party at the boss’s house?

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Some general safe bets for work-related holiday parties

The festive blazer

There are so many festive blazers in velvet this for the holidays this year! This Eliza J one is almost always also in stock, and this BlankNYC one looks great for under $100.

Statement necklace

(You can take it off or add it as needed!)

Party pants

Wear a solid color top and add jewelry to liven it up.

In 2022, for party pants, we’ll see a plethora of sequins, velvet and lace. There are so many leather pants for work that we won’t even include them in this roundup!

Party tops

These can be trickier – but these are the best we’ve seen this year.

Note that regardless of how it’s shown on the model, you should a) not wear a sheer top to an office party, and you probably shouldn’t wear a crop top or anything that exposes your stomach. Depending on the office environment, you may want to bring a cardigan, shawl, or shrug if your top exposes a lot of your arms, such as with a halter top.

Stock photo via 123rf.com / stockbroker.

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