Open Thread: Halloween Costumes for Office-Related Events

We’ve gotten a few questions inquiring about office Halloween parties (some poor soul out there is being required by her team to dress as Peggy from Mad Men!) and I thought I’d start an open thread… have you ever dressed up for Halloween at the office? Have you ever attended a Halloween party that was primarily co-workers — and if so, did it factor in to what to wear?

For my $.02… I would advise against wearing slutty costumes (or, if you do, avoid uploading them to Facebook!), as well as overly political things, or interactive costumes (e.g., anything involving a squirt gun), or even overly silly/childish things (e.g., dressing up as a character from a book or show that is known for being enjoyed by anyone under 18).  In other words: Halloween is really, really hard to do right at the office.  But maybe I’m wrong… ladies?

Pictured:  I recently saw this old story (“Bank Intern Busted by Facebook”)  linked to again so it’s fresh in my mind…


  1. Anon for this :

    UGH. At my old firm, Halloween was a very competitive affair, with people forming secret teams and devising elaborate group costumes for months ahead of the annual costume party/potluck. Costumes were guarded with confidentiality levels usually reserved for the highest-profile of clients. And the “costumes” often involved skits, singing and/or dancing. We were absolutely required to participate, and it was, in a word, awful. It could have been fun if it was an overall happy place to work, but it was Biglaw-esque (meaning, mid-size in number but ran itself like Biglaw) so everyone was pretty much miserable and terrified all the time. SO glad I don’t have to do that anymore. Now I can enjoy Halloween again!

  2. My firm has a pretty low-key costume contest, but I’m just as happy that my vacation coincides with Halloween this year. Way too much awkwardness inherent in any costume choice with the risk of looking like a spoil sport if you don’t participate.

  3. Anonymous K :

    I agree, Halloween is so hard to get right at the office. (Luckily, we don’t dress up at my office. I will probably be attending a party with some co-workers, but it will be the co-workers who I also consider friends, so I’m not too worried about my costume.)

    Although being required to wear a costume is, well, odd, I can think of a lot worse things that having to dress as Peggy from Mad Men! If you don’t mind blending in with the crowd (or if you want to blend in with the crowd), I think anything Mad Men inspired is a good bet this year. Other than that, I’m at a loss as to what to wear at an all-work costume party.

    I think your rules are good, Kat, with one exception. I don’t see anything wrong with some (emphasis on some) costumes that are based on children’s shows. For example, two years ago, several co-workers and I went to a party together dressed as the Scooby gang from Scooby Do. It wasn’t at a work sponsored event per se, but it was at an event that was attended by many co-workers and most of our superiors. Our costumes got a generally positive reception (we actually won for best group costume) and I don’t think we were perceived as silly or childish. I mean, part of the fun of Halloween is being a little silly! I do think dressing up as say, Dora the Explorer, would be perceived as childish. Perhaps the main difference is that Scooby Do is a classic cartoon? At any rate, I think the dressing up as characters from a kid’s show can be done, but must be done carefully!

    • ha! OK, I like that. I guess I’m thinking more of things enjoyed by *current* teenagers, not stuff we enjoyed while growing up.

      I would also caveat it with “You’re allowed to dress as __ if your kid is a huge fan of __ and you’re already dressing up for some parent-related activity like trick-or-treating.”

  4. In the past I have stuck w/ a partial costume. For example, work appropriate black pants and red dress shirt with devil horns and a tail attached to my belt loop. Or black pants, black shirt and witches hat. However, I was working with “sexually deviant adolescents” at the time, and some of my coworkers questioned my choice to wear the “devil tail” as it could draw comments such as “nice tail.”

    I am at a total loss this year of what to wear even to an outside of the office, just friends, party that is not entirely slutty, still kind of fun, and not a $500 costume you would see a character at Disney in. Ideas?

    • You could wear a suit + witches hat & be Christine O’Donnell. Assuming you know your audience, of course, and know that you won’t offend anyone or start any political skirmishes.

      • Heh, this would go over GREAT at my workplace.

        • White blouse, black pants, $5 tri-point hat, $2 eye patch, maybe spring for the $8 plastic sword — instant pirate.

    • My go-to not slutty outfit is Carmen San Diego. Red trench coat, red pants and black boots. It was simple, cheep and everyone loved it.

  5. Thankfully, I have never worked somewhere where we were expected to dress up for the office. Whew!

    I have to say, the most fun Halloween party I ever went to was a party in the village (NYC) when I was in law school – I wore a long red vintage (50s) red and gold tapestry dress and a fancy butterfly mask from New Orleans. At the party I was the only classily-dressed girl! Then on my way home a couple of people asked to take my picture. :)

    • so…what were you?

      • Super cool looking. Didn’t really matter what I was. :)

        • Anonymous :

          I actually kind of hate that. Obviously everyone has the right to do whatever they want, whether on Halloween or on a random Tuesday, but the whole point of Halloween is not just to wear whatever you normally have no occasion to wear. You’re supposes to dress up in a costume. So if you want to wear your prom dress or that sari you picked up in India, or whatever, at least be somewhat creative about it.
          I know it’s silly, but this bothers me almost as much as the whole “Halloween is an excuse to dress like a complete whore. Yay. I am going to be a sexy referee/plumber/insert your own stupid, pointless whatever.”
          Maybe this year I’ll just do an odd combination of weird sparkly dress/partially skanky costume & tell everyone I am going as a “Trite Halloween Outfit.”

          • L: Bet you were cool looking! Waa to people who hate what other people wear! I love Halloween and the people in my office dress up all the time – even when it is not Halloween!

        • From L’s original description, it actually sounded like what I’ve seen in movies/tv shows when fancy rich people are attending a “masked ball” – I love it! Very classy and fun, and a nice contrast to the lingerie + animal ears costumes.

  6. Our office has a party for children of employees of the firm. Some people dress up, although most don’t. In years past, I’ve dressed up in pretty low-key costumes, such a witch, a cowgirl, etc.

    This year my kids are attending and are dressing as part of the Scooby Doo gang. My daughter really wants me to dress up as Velma. If I can find the right red skirt and orange sweater, she may get her wish.

  7. Our firm does a big Halloween decorating contest. All the staff decorate their areas. It is very competitive and actually a lot of fun. The staff get prizes. My 7 year old loves it and I let him decorate my door and outside my office. The other attorneys in my section get a kick out of my son’s decorating so his efforts have been allowed to move to their doors. I usually don’t dress up (I have never been one for costumes) but I am this year because I actually have kind of a low key but funny idea. My firm is New Orleans based so costumes are not unheard of (you should see what they do for Mardis Gras). We have male partners who have been known to dress in a dress.

    We also have a Christmas decorating contest.

  8. Dressing up for Halloween at the office? ::::SHUDDDDER:::::: I have enough trouble with that in my regular life!

    That said, I would probably throw on a Patriots jersey and say I’m Wes Welker. So boring, and yet, so inoffensive.

  9. Oooh, Kat, I disagree with you very much on dressing up as anything remotely related to a real-life mothering role!! It’s hard enough convincing people that you are serious–perhaps even more than before–about your job now that you’re a parent. Reminding them of the little one in your life at party time would just give them more reason to think of you as the mama, and that there is nothing else to you.

    I’d go classic–witch (dress in black with lots of green eyeshadow), mad scientist (basically a lab coat & glasses), headless goblin (cardigan over your head, jack-o-lantern under your arm), etc–to stay safe and still be seen as “fun”.

  10. Thank goodness nowhere I have ever worked has had anything other than candy to celebrate Halloween. I did, however, have a client meeting one year on Halloween. We all showed up at the client offices in business attire, and everyone there was wearing … pajamas and slippers. It was completely bizarre. I know I can be fuddy-duddy, but my view is that Halloween is for children and consenting adults, not for an office.

    • This happened to me once, but it was a job interview! Picture being interviewed by a clown. Seriously. I have never completely gotten over it.

      • Ha! I had an interview on Halloween once and was interviewed by a woman in an Underdog costume. And that was the highlight of my day. It was pretty much my worst interview (and Halloween) ever.

        • Wow. Of all the characters to pick–Underdog? What was she saying about herself, and how did you ever keep from laughing?!

  11. Reality check please! I am contemplating going as a new, overworked attorney (read: no costume). Is that only funny to me?? Because in my sleep deprived delusional state I really can’t tell anymore …


    • Overdo it with a couple of details–goofy glasses, a legal pad, nametag with a goofy name explaining the non-costume. When someone asks, smile and say it’s a costume, not you, because you’re having such a wonderful time in your position.

    • Anonymous :

      When I was a 1L, I attended a halloween party wearing a t-shirt that said, “1L” – that and a pair of jeans was the whole costume. Some people said it was a cop-out, but I got a few laughs. What about doing iron-on letters on a t-shirt that just says the name of what your “costume” is: “Clown,” “Cowgirl,” “Witch,” “Vampire,” etc. I think most people would get the joke (like, ha ha, I’m too busy for a costume so this is the best I could do) but I suppose you could also be seen as a spoilsport or a complainer…

    • In law school my classmates regularly dressed up as our professors–signature crazy hair/bow tie/ugly sweater and all. The profs generally took in in the spirit intended–as affection.

  12. divaliscious11 :

    Ack..I have a non-work Halloween party that I need a costume, but don’t have any idea what to be. I am swamped at work, down a person on my team, trying to finish my MBA, and trying to find a costume for picky 7 year old who didn’t want anything she saw when she went out with Dad last weekend! Any ideas i might be able to pull out of my wardrobe????

    • Pick a well known political or business figure whose wardrobe resembles yours (Sarah Palin if you tend toward bracelet length jackets and pencil skirts; Hillary Clinton if you tend towards colored pantsuits; Condi Rice if you like knee high boots, etc.) and go as her.

    • Put on a hot mini, with some smokin stilleto’s, add a long blonde wig and BAM, you’re Tina Turner.

    • Gypsy? A big bright shirt of yours, her biggest pants, lots of your long chains, some make up (which is always fun for kids) big hair, pin some little bangles (cymbals from a craft store) to the bottom of the shirt?

    • Diva, check out my ideas for costumes a few posts up. I think they’re all pretty simple. You can spice any of them up easily–I once went as a pharmacist by wearing a lab coat, stockings and white stripper heels.

      For the 7-yr-old: find a box big enough to fit over her head & cut arms for her arms & head. Attach 2 rows of margarine tubs down the front. Spraypaint the whole thing and have her wear pants/ls shirt of the same color or black. Tada! She’s a Lego block. If you want to go for overkill, stitch some real Legos to a knit cap.
      If Legos don’t do the trick for her, I’d suggest googling diy kids’ costumes with her. Don’t do any of them exactly, but let them spark her imagination. My son was a great frog prince for fairy tale dress up day at school–I found out the evening before–with green clothes, a crown he made himself, and a great smile. The headband with googly eyes and other doodads the site suggested were unnecessary in his book.

      • My mom made me dress up as a present when I was in elementary school. The next year she decided that I would go as a single die and she used the same box, painted it white and put black dots on it and my armholes counted as 1 black dot. I’m still traumatized from these costumes.

    • White sheet with eyeholes. Bam, you or your kid is a ghost. Lazy? Yes. Effective? Absolutely.

      • (If you have gladiator type sandals, put some ferns in your hair and wrap the same white sheet over a tanktop and leggings or shorts toga style and BAM, Roman senator.)

      • Pjbhawaii :

        Naw, too much like the KKK.

        • No, KKK has a pointy had. Roman senator has an olive wreath. Headgear is distinctive.

    • Snooki from Jersey shore? Tan in a can, fuzzy slippers, too tight dress and a solo cup.

    • divaliscious11 :

      Thanks for the tips…. I’ve never watched jersey Shore, not sure any of my friends have, but that might be easy…. and comfortable (slippers!)

    • one year, i dressed up as a christmas tree (green dress, brown tights, garland in the shape of a star on my head, draped in tinsel, etc) and my friend dressed up as a present (all red outfit + a gold bow over shoulder and around waist, bow in her hair as a headband). it was easy, cute, and we got a head start on buying christmas decorations :)

    • Get a pair of wings ( and both have some nice ones) and throw on with a cute little dress or skirt. Tada, you’re a fairy! (Wand optional)

    • How about Legally Blonde inspired (even if not blonde)– similar style suit in a pink/pastel shade, super high heels, cute hair do, and a (stuffed toy) puppy peeking out of your purse.

    • S in Chicago :

      Green dress (or anything retro) with a short blond wig. Pin on some birds from the local craft store and–voila–you’re Tippi Hedren from The Birds.

    • Diva – go as Audrey Hepburn from Breakfast at Tiffany’s…black sheath, loads of pearls, and cigarette holder. Don’t forget the Danish!!

    • When mine children were young and didn’t like anything, they went as a bag of jelly beans. Clear plastic trash bag (yes, you have to cut a hole in the top for the head) and holes on the side for arms. Stuff it with little colored balloons (that the siblings had to blow up) I sent my oldest to a school costume party as a salad bar… I made a large circle with cardboard, cut a hole in the middle for her to fit, fastened straps from the front, over her shoulders to the back. I then glued plates and bowls of veggies all over it. She won first prize and everyone ate healthy!!

  13. OrgManiac :

    While on vacation in Ashland OR this year, I found a shop that specializes in breezy, swingy things, and bought a multi-layered skirt with jingle bells sewn on … I’m going to add a camisole, and bought several cheap scarves from Affordable (thank you, Corporette, for the tip!) to wear aroudn my waist, shoulders and hair. I’ll be dressed as a gypsy or fortune teller. It’s turning out so cute, my 13 year old tried to swipe it from me.

    • oops, I replied to someone above saying “gypsy” without reading your comment. Wasn’t trying to steal it.

    • I really hate to be the PC police, but if possible, go fortune-teller over gypsy. I recently had some very patient Eastern European friends educate me on how offensive the term “gypsy” is, and even if most Americans don’t see it or intend it that way, why not steer clear.

      • Blonde Lawyer :

        Would you mind elaborating please? I thought “gypsy” was the actual term for migrant people who sold goods in the streets. Why is the term offensive?


          • Blonde Lawyer :

            Interesting. That wiki article noted that the word I learned in Spain (los gitanos) has the same negative connotation as gypsy. It did at least say “in North America the term tends to refer to a lifestyle and fashion choice.” Nonetheless, it is good to know as you never know who you are offending when you speak.

      • Thanks – I thought about commenting above with regards to “gypsy” and then didn’t… but I’m glad you did. I look at “gypsy” costumes with the same questionable-ness as “Geisha girl” or “Indian [Native American] princess” – would definitely steer clear at a work gathering.

  14. I will only go so far as to decorate my office door for Halloween. Costumes at work? —Sorry, not doin it.

  15. I’ve never dressed up while at work, but last year I went as Flo from the Progressive commercials and this year I’m going as the girl from the Orbit gum commercials. Neither are your typical overexposed costume, but I think they are fun. I got quite a few compliments on the Flo costume last year.

  16. Magdeline :

    On the Practice (circa season 2), Helen dresses up as a flapper for a Halloween party and I thought it looked really great! You can be relatively covered up and look professional and classy. (LBD, headband with feather sticking out of it, maybe some pearls tied in a knot and a little lipstick and “bam”- you’re done!)

  17. My office for years has done massive decorating for kids, kids in costumes, a few co-workers in full-on costumes. I’ve gone for the low-key approach — black pants, white blouse, black felt hat, eye patch for when the kids are around, black boots if it’s cold enough – ta-da, instant business-appropriate (if a bit boring) pirate. A costume for the hour the kids are there, a regular outfit the rest of the day. And, pretty cheap!

  18. Anonymous :

    One year, a friend and I went as “nudists on strike,” which involved regular clothes and protest signs that said “Here’s my stance: I wear pants.” Easy and you get to be comfortable.

  19. scientist :

    Luckily we don’t dress up during the day in my office, but we often (depending on how the yearly social budget is distributed) have an evening Halloween party. Last year I dressed as the waitress from Office Space: white polo shirt with basted-on green felt stripes, khakis, suspenders with a bunch of pins (courtesy of my nephew, who gets them at soccer tournaments), and a waitress-apron-thingy that I pinned together from some black fabric. Really simple, dead obvious if you’ve seen the movie, sets you up for funny chitchat (make sure you have enough pieces of flair!) and is totally appropriate – for anyone who is still thinking of a costume, I recommend this one. This year, one of the other people in my immediate group within the company is making us matching M&M costumes in various colors, so that should be interesting…

  20. Back when I was a 3L, my Crim Pro prof required her students to come in costume when Halloween coincided with class. We had to be something connected to law. My study partner and I bought some long black robes, covered them pins that said “No Nukes” “Save the Whales” etc. etc. and brought along some picket signs. What were we? Activist Judges!

  21. Another Anon :

    I usually wear an Old Navy halloween-themed t-shirt under a blazer. Everything else is “business-as-usual.”

    • Anonymous :

      I recently found a skull and bones print button down. I’ll be wearing that underneath my most conservative cardigan. :)

      • One year I wore a t-shirt that said “This is my Halloween costume” printed across the front, I added a headband with 2 springy things sticking up with little skulls on the end, and “bam”, instant sort-of costume.

      • WHERE did you find that I want it!

  22. Another Laura :

    I have family members with the same family name who are doctors so I have a white doctor’s coat with my name embroidered on it. Borrowed stethescope plus a clipboard. Worn over my regular wool pants and top. Bring my jacket to work to slip on in case I have to see a client or attend a meeting. If I wear it after work, I add scrubs and booties.

    My other default is wearing a suit (say a purple suit) and using spray-on hair color in purple! One stripe of color a la Cruella de Ville.

  23. Anonymous K :

    My easy go-to costume is Anna Wintour. She wears relatively simple dresses and shoes, so most women already have the basics. You just need to throw on some big sunglasses, a bob with bangs wig (if your hair doesn’t already look like hers), and, of course a fur coat (the one I’ve worn is faux) with red paint on it. It’s also a really easy costume to throw on post work or to take off if you’re wearing it at work and a client meeting, etc. happens to come up. I got my faux fair coat at H&M a few years back for about $20. Of course, now that it has red paint splashes on it, it can’t be worn for regular everday use, but it’s been worn on Halloween not only be me, but by several friends. (I understand this may not work at every office particularly if, say, no one at your office will understand the reference, but it’s been a hit for me in the past!)

  24. Mystery Me :

    I normally work from home, so this issue doesn’t specifically apply to me. I am, however, from a conservative culture and the bulk of our “friends” tend to be my husband’s relatives. While I wear whatever I chose in my normal life, when in front of family, I have to appear attractive, yet non-sexy (somewhat difficult because I am rather large chested… I normally look frumpy).

    Thanks for the great suggestions for conservative-ish yet cute costumes. I will def utilize these ideas this year for the multiple family halloween parties that we are invited to. No more frumpy!

  25. Audrey Hepburn in Breakfast at Tiffany’s comes to mind when I think of office-appropriate costumes. Great LBD, pearls, hair up, cigeratte holder, ta daaa!

  26. “gypsy” is a race term for people who originated in N India. They have LNG been discriminated against in Euope. Until recently, for example, they were not permitted to own land in France. They are discriminated against in employment, schooling & other aspects of daily life and are accused of being shifty & thieves. A less offensive term is “Sinti & Roma”.

    If a fortune teller or street bender is what you man, you could slays say “fortune teller” or “stret vender”.

  27. My work doesn’t support any sort of Halloween celebrations that I am aware of. I know some groups may do something, but most holidays are dismissed (although Steelers and Penguins games are embraced like the most important of holidays). Sometimes they do Ugly Sweater Day around the holidays, but most of the time, because it is such a multicultural office, it’s hard to do anything without offending someone.

    I do disagree, though, on costumes that “appeal primarily to those under 18”. Superheroes, comic book characters, and the like can appeal to plenty of people, regardless of their targeted audience, and if you work with kids or where there will be a children’s party, it’s a guaranteed win.

    I plan on wearing my Batman shirt under my blazer the Friday prior. :)

  28. I went as Sarah Palin a couple years ago. Well, it was sort of Tina Fey as Sarah Palin. Black pencil skirt, pink suit jacket, hair up, dark rim glasses. I kind of have her facial bone structure, so with heavy blush and eye makeup it worked.

    But I knew in my small office I could get away with something semi-political like that. YMMV.

  29. I have a great Cruella DeVille costume that is my go to. A black dress, red gloves, red shoes, my fun Cruella black and white super curly wig, and a cape I made out of dalmatian print fabric. It is fun, cute, and appropriate for every occasion I have ever needed it for, including work, church, and a Halloween party in Chicago.

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  31. I think that witty costumes are the best. At one Halloween party a couple of years ago, I saw a guy wearing a blue hoodie with a rubber chicken wrapped around his stomach with a telephone cord. He was ‘chicken cord on blue’. I’ve wanted to do it ever since.

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