2015 Update: We still stand by this advice on what to wear to the boss’s holiday party — but you may also want to check out our more recent discussion on what to wear to a holiday office party.
The intimate office holiday party at your boss’s house: it’s like it’s designed for trouble. What the heck do you wear? Reader J wonders this very question, and asked us what to wear to the boss’s holiday party…
I work in surgical research, and although this is a very different field than most people who read this blog, my work environment isn’t all that different when we’re not in the operating room- business casual, long hours, small division (within general surgery). I’ve worked here about a year and a half and am the youngest staff member here by about 20 years (I’m 23). My question is- what do I wear to a small, conservative Christmas party at the Chief of the division’s home?
We’ve talked about whether to bring a hostess gift, how to save money on fancy attire, and how to look professional in an evening gown — but we haven’t talked about what to wear to the intimate party at your boss’s house for a while, so let’s discuss. In my mind, you need to ask yourself a few questions. The primary one is thus: Who can you ask? If you feel uncomfortable asking the men you work with, ask a female coworker or two. Note that the answer, “My wife is wearing __” is not necessarily what you should be wearing, since you’re there in a different capacity. For example: if the wife is wearing a sparkly, strapless cocktail dress, you should probably wear a more conservative but still festive dress (such as this, this, or this), or perhaps one of the great “party pants” (such as this or this) we’re seeing this season with some killer heels and a sparkly sweater. The same thing goes if the secretary for the group says, “I’m wearing jeans and a funny holiday sweater!” You need to dial it up a little bit from that — perhaps a festive blazer with a pencil skirt or sheath dress.
If you really can’t ask anyone, ask yourself a few more questions…
1) Is the party on a weeknight or a weekend? If it’s a work day, odds are good you’ll just wear a slightly more dressed up version of what you wore to work that day.
2) Are dates invited? If dates are invited the equation changes only slightly — in my experience, it makes it slightly more possible that people will be dressed up.
3) Are staffers invited? If the entire team is invited — secretaries and assistants — you need to keep your outfit more of a dressier version of what you wore to work. Especially if you’re younger, you don’t want to lose any “professionalism” points with the staff. If you’re on the fence about your outfit, ask yourself: “How would I feel if someone wearing this outfit asked me to do X, Y, or Z?” (insert common tedious/unpleasant tasks there). If the answer is “ANGRY,” change your outfit.
If all else fails, think “classic beauty” when putting together your outfit — veer as far away from “sexy” as you possibly can.
Readers, how do you figure out what to wear to the boss’s holiday party? Have you ever seen any wild fashion gaffes at such parties?