What to Wear to the Boss’s Holiday Party

The intimate office holiday party at your boss’s house:  it’s like it’s designed for trouble.  What do you wear?  Reader J wonders this very question…

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.  (Pictured.) 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.

-------Sponsored Links--------

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?

Share on FacebookTweet about this on TwitterShare on LinkedInShare on Google+Pin on Pinterest


  1. This year’s holiday party (in Chicago finance) was announced to me like this: Oh by the way the holiday party is tonight. So.

    I wore what I wore at work – charcoal cords from Banana, a dark teal mandarin collar buttondown from Loft and a black Zara blazer and just was thankful that I’d decided to wear a pair of my more fun earrings to work.

  2. style advice needed... :


    Belts. Where’s your favorite place to by a good, classic, quality belt? Especially in light of holiday sales… Links to your favorite belt are appreciated.

    And with the variety of pant waists these days (higher, lower, very low rise..), I find that the same belt does not work on multiple pants very well. For example, it can look not very nice to buy a longer belt that works when it falls lower, but then it has a long floppy end when you wear higher rise pants.

    My waist is small. My hips are full. I’m not even sure where to measure to choose a belt these days.

    • I have multiple belts and wear them depending on what the belt is used for (i.e. skirts, low waist pants, high waist pants, dress belting, etc). I honestly buy from Target or the sale rack. For fun, showy belts (meaning for looks only, not function), I have skinny ones from J Crew.

      • style advice needed... :

        I am jealous of your belt collection! My wardrobe is quite small at the moment, and it will take awhile for me to build up a belt collection. I am hoping to buy 1 or 2 good belts that can last me at work while I build my my staple/higher quality wardrobe.

        Otherwise, I probably last bought a belt at Marshall’s many years ago. None of them last, and they always look a bit cheap.

        I’ll look at J Crew. Thanks.

        • Moving to the City :

          I bought a brown J Crew skinny black leather belt and a dark brown leather belt and had a cobbler add holes (I think that I gave him $2 or something) so that I could wear it with more pairs of pants. They’ve held up fine so far.

    • Miz Bizcuit :

      I’ve had good luck with woven leather belts, the kind without holes. You poke the buckle prong through the weave of the belt, so they’re infinitely adjustable. Great for weight fluctuations.

      • style advice needed... :

        I like this idea. Do you have a link to one you use?

        • Miz Bizcuit :

          Wide Woven Belt:

          Narrow Woven Belt:


      • I have a belt like this that’s actually a hand-me-down from my mum, it’s fab! With normal belts I always end up with them slightly too small or slightly too big.

    • Talbots has good quality belts (I have several). Check out their sale section (Talbots.com, select “Sale” in upper right). AND they are having an extra 40% off EVERYTHING right now.

  3. I bought a black velvety type blazer and I have been wearing that with everything. Dressed up but clearly fun, and lets me get mileage out of fun clothes I wouldn’t wear to work otherwise. Also dresses up a boring outfit so I’m not the creepy one in all matte black. I also keep flashy earrings in a pill box in my purse.

    • I have a black velveteen blazer that I love for this time of year. I like that it’s luxe but laid back at the same time.

      Men really seem to like the velveteen blazer…though perhaps a little *too* much. I keep getting comments on it from men who wouldn’t/shouldn’t ordinarily comment on my attire. Is there some hidden message I’m sending? Is velveteen too sexy for business? I’m confuddled.

    • TO Lawyer :

      Where did you ladies get your velvety blazers? Our office party is next week and I’m stumped for what to wear

      • Mine is Talbot’s from last year. This season I’ve seen nice ones at Ann Taylor, Talbots, and Cache’.

  4. I was at just such an event last night – a post-office hours holiday reception held by the boss at their home, & there was a pretty obvious uniform. Everyone was coming from the office, so that impacted the dress code. For the older women, the festive suit. Me – black velvet blazer, silk print shell underneath & a pair of black dress pants. Others – festive jacket, brocade, velvet, tussar silk or similar, St John knits with a sparkly trim or thread in the fabric, paired with coordinating dark pants, a skirt or sheath dress. The younger crowd were pretty much uniformly in office appropriate black or dark solid color dresses that they dressed up with some sparkly jewelry, a statement necklace or cuff or earrings & maybe a dressier shoe.

  5. i talked about this in a recent blog post:

    at your own party you should dress a bit more conservatively than if you are a guest…

    with that in mind, i think a high-waisted skirt, opaque tights, and a high-collared shirt (maybe a turtleneck or cowl-neck?) would be appropriate..

  6. My experience with these parties (law firms, both big and small) is to dress like you are going to a nice dinner. I would either wear black satin tuxedo type pants with a dressy top and dressy heels or a cute dress.

  7. Research, Not Law :

    I’m in medical research. I usually wear black slacks, a jewel-tone sweater with subtle ‘festive’ flare (beading around neckline, glittery buttons, etc), and jewelry with a bit more bling that my usual. Most people wear what they would wear to work with a little holiday touch.

    My boss and his wife request shoes off at the door, so I don’t wear a skirt to avoid pantyhose feet.

    • Excellent point… when going to someone’s home for the first time, you must consider that you might need to remove your shoes. All the more reason for that holiday pedicure. Or cute socks.

    • Wow. It takes a special arrogance to have a party and make your guests take their shoes off.

      • Why? It’s customary across Asia and many of my friends of Asian descent here in the U.S. request this in their homes. If I’m a guest in someone’s home, I don’t have a problem adapting to minor requests like this.

      • I agree; but it is not uncommon in certain regions. I was shocked when I found out that all my Canadian friends expected everyone to doff their shoes at the door.

      • I totally disagree! Its the norm in Canada. I hate trooping through someone’s home in my shoes (especially if there are children!) and although of course I do it when I’m in the states it always seems very strange to me.

        I think as a guest its your role to adjust to your hosts customs and preferences, especially if they are so minor. I don’t consider this an “arrogant” request at all, perhaps just one that it culturally unfamiliar to you.

        • Saacnmama :

          We take our shoes off in the house, and when we have a guest or two over, they are asked to do the same. But a party, with lots of people, is going to require setup and cleanup anyway, regardless of whether peoe wear shoes or not, so I wouldn’t ask. Besides, we don’t have shoe storage space for 30 extra pair.

    • emcsquared :

      In the Midwest during winter, everyone takes their shoes off because they are probably covered in snow/salt/grime from even a short walk from the street to the door…so sometimes it’s a practical thing too.

      • Exactly. Its why for these sorts of events I often carry a pair of velvet slippers to change in to at my hosts. Its the height of rudeness to trek around someone’s home in muddy shoes.

  8. I also work in a division of general surgery and am one of the younger and newer members. We just had a holiday party at one of the surgeon’s houses on Sunday evening and I had stressed a bit about what to wear since it was my first such event here. Keep in mind, I am in Seattle, where socks and sandals reign. Most of the providers took the opportunity to wear (dark) jeans but dressed it up with sports coats over polos or sweaters. Most of the women looked like they were wearing what they would normally wear to work. Some had black dress pants and a sweater with some sparkle. I wore a black v neck dress that I scored at a Barney’s sale, which has elbow length sleeves and comes to right above the knee. I wore black sheer stockings and a pair of black patent perfect pumps from ann taylor and simple diamond jewelry. My husband wore a maroon button down dress shirt and gray dress pants and we were the most dressed up couple there, but not uncomfortably so.

    As far as wearing high heels, keep in mind that you are going into someone’s home and they may not want you walking around making divots in their hardwood floors. I was sure to wear black sheer stockings with sheer toes just in case I needed to remove my shoes!

    • karenpadi :

      Second the advice about not wearing stiletto heels in someone’s house. To avoid creating divots in hardwood floors, wear heels with thick “posts” (what is the word for the ankle end of the heel?), wedges, or flats.

  9. Going to the hubs’ small office party tonight. I’m technically a wife, but they know I’m also a lawyer, and coming from work. Black pencil skirt, subtle sparkly sweater, black velvet blazer, black patent leather pumps.

  10. I am completely at a loss here. NEVER in a million years would I think that I couldn’t wear a certain pair of shoes to a party. Wow. Just Wow.

  11. I have this dilemma always

  12. Don’t wear anything too revealing. You can look elegant and sexy in a nice way. millinery

  13. Thanks for writing such an easy-to-understand article on this topic.