What Should You Wear to a Work Vacation Party at Your Boss’ House?

We asked a few weeks ago whether company holiday parties are held This year and many of you have said that the holiday party will be something smaller at your boss’s house 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’s house?

This will obviously vary based on your career, company, position and relationship with your boss – but I think overall there are some things to consider.

What Should You Consider Before Choosing Outfits for Work at Your Boss’ Holiday Party?

shoes. When I go to a house party, I’m never sure if the host will ask us to take off our shoes – which is why I hate wearing a shoe-tied outfit. For example, if you planned to wear over-the-knee boots, think about the outfit you’ll be putting together – and then remove the boots.

Sometimes even with tights I will layer them with a pair of socks under the boots, which feels equally awkward to keep wearing the boot socks as well as removing the socks with the shoes. If you’re wearing socks or stockings, consider how well-groomed they are and whether there’s anything in them that you wouldn’t want your boss or people at the party to see. (My “bring wine if you can read this” socks probably wouldn’t have made the cut.)

Even if you wear shoes, I could see some stilettos being difficult to put on, snagging on looser carpets or rugs – so if you’re prone to snagging, these might not be the shoes for you.

How casual or stylish. This is always deceptive and I would probably go middle ground unless explicitly stated otherwise by a dress code. Holiday-colored pants and sweater: yes. Jeans and a sequined top: maybe? (Ugly Christmas Sweater: maybe!) Leather pants – get to know your office.

(Skirts and dresses go back to the question of shoes for me – I think heels are an integral part of these outfits, but your mileage may vary.)

Heat. This may be a “me” issue, but I hate being cold as much as I hate being hot – so I’d dress in layers. Many homes get really hot if there are a lot of people inside – but to make up for that (or make the party more COVID-friendly) you can have windows or doors open, which can make the environment uncomfortably cold. (Or everyone’s favorite: stifling hot in some areas and cold in others, depending on the way the air moves through the house.)

Hair and makeup. I would probably pop in and pull off my party makeup for a bang or a fun updo for this occasion. If I’m going to eat or drink something, I usually try to focus on the eyes instead of the lips but maybe this is me.

Consider lighting. One final note: yes, you can come across some bad lighting. Hosts can have harsh overhead lighting that will cause (for me at least) my makeup and outfit to look different than it would in a more subtly lit space with lamps. (It may also make some fabrics more sheer or otherwise revealing in terms of panties or cellulite (you should care about both).) If you haven’t been before, you really have no way of knowing…

How Do You Know What to Wear at Your Boss’ Holiday Party?

when we last discussed That said, I noted some more questions to consider with the guidelines – I’d say they still apply:

• Is it weekdays? Wear straight business attire, but you can swap it out for festive jewelry, a sparkly sweater, or a velvet blazer.
• Have support personnel been invited? Depending on office dynamics (and often do you feel too young/not taken seriously by support staff), you may want to keep things more business side.
• Are there any plus-ones? This is a general hint that the Forces are willing to loosen up a bit, and festive attire may be appropriate.
• Are the children invited? Stay away from anything too fancy.

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

(The comments in the original post are fascinating – both If you are a plus one, how would you consider dressing up for a holiday party?clothes like sheath dresses and black suits that feel a lot more formal than I can imagine (most) people currently wearing.)

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

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Some General Safe Bets for Work-Related Holiday Parties

Festive Blazer

THERE’S A LOT festive blazers velvet for the holidays this year! This Eliza J one is almost always in stock and this emptyNYC one looks great for under $100.

Description Necklace

(You can remove or add as needed!)

Party Pants

Wear a solid colored top and add charms to liven it up.

We’re seeing tons of sequins, velvet, and lace for party pants in 2022. There are so many leather pants for work that we’re not even including them in this roundup!

Party Tops

These may be more misleading – but these are the best we’ve seen this year.

No matter how it’s shown on the model, a) you shouldn’t wear a sheer top to an office party, and you probably shouldn’t wear a cropped top or anything that reveals your navel. Depending on the office environment, if you have a top that leaves most of your arms exposed, such as a halter top, you may want to carry a cardigan, shawl, or shrug cover with you.

Stock photo via 123rf.com / stockbroker.