What to Wear to a Big Meeting at a Casual Office


2017 Update: We still stand by our advice for what to wear to a big meeting at a casual office, but you may also want to check out The Ultimate Guide to Business Casual for Women.

When you work at a company with a casual dress code, how should you step it up for a board meeting — or for other important meetings — when you want to look professional but don’t know what others will be wearing? Reader A wonders…

I have a fashion question: How does one dress for the board meeting of a “casual dress” company? We are a start-up — this is our first board meeting — so I really don’t have a precedent to call on. During a normal work day, my boss (the CEO, age 45+) and I typically wear jeans and a sweater or T-shirt, as we only have phone/email contact with clients. However, it seems like the board meeting calls for a more professional look. I asked my boss about it, he said “What you’re wearing is fine.” (Faded jeans, a long-sleeved Tshirt and a scarf.) He is not the type of guy I would normally take fashion advice from, and I’m not sure he fully understands the nuance of female dress! Most of the other officers and board members are lawyers, lobbyists, or CPAs. I don’t want to show up in jeans, but I don’t want to be the only one in a suit either. Is there something inbetween? Dress slacks and a cardi? I am age 35+, and a size 14 (XL), so I don’t want anything too clingy or “young”. Suggestions?

We’ve talked about how to do business casual without looking overdressed, a casual-but-professional uniform for womenwhat to wear to a casual office on your first day, shoes to wear with jeans at work, and more — but not this.

Interesting question, A, and I’m curious to hear what readers say. For my $.02, I would avoid the “dress slacks and a cardi” look when everyone else is in jeans because you inevitably end up looking like the mom of the group. So I’m going to offer you two suggestions and suggest you go with the one that feels right — but again, I’m curious to hear what the readers say.

A) Jeans and a blazer, preferably either with sleek heels or personality sneakers like Chucks or the New Balance x J.Crew sneakers that everyone has. Think confident! Think cool!  Try adding a statement necklace or a scarf to the look, or try pushing up the sleeves of your blazer. On the shoe point, I am thinking of two different kinds of women here — one is sleek and sophisticated; the other is cool, smart and confident.  (Note that the latter can also be a lot harder to style — like I said, go with what you feel comfortable with.)  You can wear other shoes, of course, but the margin for error is greater with flats, boots, comfort shoes, or others. Stick to neutral colors if you’re in doubt, with a pop of color somewhere — possibly just a red lip. As always for business, look for jeans in a dark rinse with minimal distressing.

B) A sheath dress and, again, sleek heels. This is another suggestion based on the margin for errors — the “it” business dress is pretty much a no brainer. Sheath dress, black or beige heels, and if you think you might be cold or aren’t happy with your arms in the dress, bring both a cardigan and a blazer to work that day and choose your topper based on what the guys are wearing. This is more of a dressed up look, for sure, but a common one among women in techthink Sheryl Sandberg. It does say that you’re the grown up of the group — but it doesn’t suggest you’re taking lunch orders or doing other office housework.

Ladies, what would you wear to a “big meeting” in a business casual environment? How would you decide?


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  1. I would definitely wear a blazer but I’m probably biased because I love blazers and feel like they’re the ultimate power piece.

    In the alternative, I like Kat’s idea to wear a sheath dress.

  2. I work at a male-dominated company and in situations like this, I wear a dress because the men I work with don’t know if it’s formal or casual – they don’t really get how dresses work. A dress with a blazer could go either way.

    • This made me LOL in agreement – “they don’t really get how dresses work”

      • Anonymous :


      • Frank know’s how dresse’s work. He is constantley telling me that my dress is loose, or that he could help zip and unzip my dress for me. FOOEY on men that want to take our clothe’s off. And he is MARRIED. I think that if I EVER took him up on it he would realy pee in his pant’s, b/c he would have to explain to his pretty wife that he took some of my clothe’s off. FOOEY!

        As for the p’ost, I alway’s dress formal when I go to my cleint’s for meeting’s even tho my cleint’s are all informally dressed in the supermarkit and the cleaneing industrie’s. I think they pay more atention to me when I dress niceley b/c I am an attorney, duly admitted to the court’s of the state of New York, and they respect that. YAY!

        The manageing partner come’s with me b/c the offices are NOT in good part’s of town–one is in Queen’s and the other is in UPPER Manahattan or mabye the Bronx I think where you do NOT want to go after dark–even tho there is a great Chirpin’ Chicken place up there that Roberta get’s take out for us from. FOOEY on the neighborhood. But Roberta pay’s her bills VERY promptley b/c we get rid of nearley all of the cases she give’s me. DOUBEL YAY!

        I asked Myrna if she wanted to do Seder with us–her family lives in the mid-West and she like’s our customs, so she said yes. Dad will be thrilled b/c he will be abel to point to her every time I eat a Matza or something and ask me why my tuchus is not like her’s! FOOEY on that, but I told Myrna and she helps me out by telling him that she has different mid-West DNA, while my DNA come’s from the old country where women were viewed more highly if they had large tuchuses. I hope it work’s b/c Rosa has a nice tuchus and she is my SISTER. FOOEY!

    • This x1000. They really don’t get how dresses work. My clients include startups and I wear dresses all the time.

    • Blazer with sheath dress is my go to power outfit in all but the most formal business situations.

      • Suiting dress with matching suit jacket is my power outfit in the most business formal situations. I need more solid color, simple sheath dresses for the less formal business situations.

  3. I’m for option A: modern and confident. Actually, I vote for a leather blazer (if you don’t mind plunking down some cash). They look incredibly chic and put-together to me. An image search for leather blazer can generate some ideas (just ignore motorcycle jacket outfits).

    • Something like this, only without the night-dress styling (and about 20% the price).

    • Agreed wrt the leather blazer. I have two: black and creamy beige-ish. Both are super versatile and worth the money. For some reason, they also work really well for meetings in Germany (and possibly other European countries).

      • I was also going to suggest a leather jacket. Otherwise, I’d vote for an expensive and/or designer blazer. I think you want something that says both “style” and “substantial”.

  4. Does anyone else think it’s hilarious to recommend jeans and chuck taylors OR a sheath dress? That’s going from one extreme to the other! I understand this whole question is a YMMV one, depending on the office but it seems very weird to say slack and a cardi are a mom look but a sheath dress is OK!!!

    • I’m sympathetic because this situation is incredibly hard to navigate. Some people in tech think visibly dressing up is a sign of incompetence (too much time spent on frivolous pursuits) while to other professionals (eg lawyers) it shows you know the rules.

    • S in Chicago :

      I think it’s easier to get the Chucks wrong than to come across too frumpy/mom. I work with a lot of financial executives and that would not go over at all. Personally, I’d go with a wrap dress in a solid color paired with an interesting necklace if you’re trying to look artsy/creative/cool and still blend well with an audience that potentially is made up of folks in suits.

    • It actually makes sense to me. There is nothing powerful or authoritative about a cardigan. To me, it’s the exact opposite as a garment and to the extent that I wear cardigans it’s usually to tone something down either in formality or impact. A blazer is the opposite – where a cardigan tones something down, a blazer tends to elevate whatever you are wearing. So to me the idea of jeans and a blazer with interesting shoes (pumps or cool sneakers or – I would add – cool, pointy loafers) works for the casual yet important meeting.

      A sheath dress – while I personally think it works less – also makes sense because a sheath dress is also a power piece. Another dress might not have the same effect and even the “wrong” kind of sheath (too fussy, too embellished, the wrong color … ) could easily be a miss. I also wouldn’t wear the dress with most high heels. It’s too stuffy and if the OP is in faded jeans and scarf at work most days, it will seem out of place.

  5. I agree with both TO Lawyer and Anon. Wearing a dress is extremely easy and looks great while adding a blazer puts that extra bit of polish to the look-successful, confident. Good luck!

  6. My variation on this is slim cut black or other dark pants that aren’t jeans (e.g., gap true straight, some of the BR sloan cuts) with flats and a blazer. Ideally the blazer has some interesting detail, or else I’ll wear a patterned shell or scarf. I’ve managed to feel comfortable in crowds wearing jeans and suits (and yes, I’ve had work circumstances in which I’m not sure which of these extremes I’ll encounter).

  7. Dress idea is the safest.

    Another option would be a skirt, top, and blazer. But play with colors and patterns to make it seem less formal.

  8. Contracts :

    I would skip the sneakers – a colorful ballet flat or pretty heels with jeans. Instead, define your style with accessories as a way to dress up your jeans and blazer or dress. A colorful long necklace with a neutral sheath or a metallic statement necklace with the jeans and blazer. Show your personality while stepping up your everyday wear for the bigger occasion.

    • Yes, go with a nicer, more polished version of your everyday clothing – especially if everyone else will be taking the boss’s lead and not dressing up. Being the only one dressed up always feels uncomfortable to me. (Unless the OP is presenting at the meeting, which isn’t clear from the letter).

  9. Meg Murry :

    Is this an all day or multi-day board meeting or just a few hours? I noticed OP said the board members and officers are lawyers, CPAs and lobbyists, which makes me think they probably wear business formal most days, (or one step below that), so I would want to step it up to their level, especially if it’s the kind of meeting where they are coming from their day jobs. I personally think dress slacks and cardi sounds ok, or this would be a good time for a knit blazer, IMO.

  10. When I know I will be significantly outnumbered by men, I never wear a dress or short sleeves (NYC Finance). In this situation I would wear black pants with either a non-iron button down shirt or a v-neck sweater, definitely coupled with a feminine cut blazer in a conservative color or pattern (but not black).

    My company has business casual but no denim or sneakers (ever) and no sleeveless shirts allowed.

    • I agree with this – Midwest engineering setting, but same rules and very male dominated. I was really surprised by the sheath dress suggestion, because even in my ‘business casual plus’ environment it would be viewed as super-dressy (because, you know, it’s a dress.) A lot of other people thought it was a great idea, though, so it probably DOES work some places.

      I’d wear the slacks + cardi, myself.
      Today I’m wearing a linen blazer with dark jeans, a flowy dark top, and heels. That might work in the OP’s setting, too.

  11. I work in an office like this. Sneakers are OK for everyday wear and for some clients (because they’re really casual). Making sure the sneakers are in good shape and look “new” is important. (Not the ratty old sneakers you use for chores, nothing that makes you look like you came to right from the gym.) Chuck Taylors, not surprisingly, are a popular choice.

    Besides sneakers, most women wear nice flats — either shoe or boot — and tall boots (flat or heel), even for dressier clients, are considered dressy.

    When the attorneys come in, we generally step it up, but most employees don’t match them on their level. It’s a good day not to wear jeans and a band t-shirt.

    If I was the OP (I’m plus-size), I would wear great fitting trouser jeans, a flat or slightly heeled boot, a great top (shell or button-down, if you have one that fits perfectly), and the blazer with the sleeves rolled up — much like Jennifer Aniston up there. Alternatively, I’d switch out the blazer for a shell, cardi and scarf combo.

  12. I have worked in offices like this, and for a Board meeting, I’d dress up compared to the t-shirt, jeans, and flip flops of daily wear. I would suggest nice, dark colored jeans and a blazer. You could wear a cool t or a short sleeve solid color shirt underneath, and I’d also add a scarf. This was my uniform for meetings with partners or Board members. I’d suggest NO sneakers; instead, wear knee high boots over skinny jeans, ankle booties with bootcut jeans, or ballet flats with ankle length jeans. You could also wear boat shoes if they’re popular in your area. I also wear this look for travel.

    I think a sheath dress would be overkill.

  13. Hope this isn’t a threadjack, but where does one buy trouser jeans these days? Specifically, I would like ones that are curve-friendly (I’m very hourglassy, and I find that jcrew type places don’t fit / flatter me) and that have button or slit pockets rather than patch pockets on the butt (not sure I’m using the right vocab, but I want ones where the butt looks a bit fancier as well, not just standard jeans pocket).

    • Talbots

    • I bought a pair of Lucky jeans at TJ Maxx. They were 1-2 sizes larger than I normally wear. I don’t know if Lucky runs small or if that is why they were at TJ Maxx.

      I actually only tried them on because I needed to see how a particular shirt I was going to buy would look w/ jeans. The jeans actually were the dream pair I had been searching for my whole life (despite the number on the tag) and I bought them at a great price. One of my favorite finds. I also bought the shoes I tried on to see “how it would look w/ heels.” The shopping Gods were smiling on me that day.

    • lawsuited :


    • Lee has nice, cost-effective trouser jeans this season. And there are a LOT of nice options on Net-a-Porter if you shop designer.

  14. If a sheath dress seems like too much of a departure from what you normally would wear, I like the idea of a fitted jacket/blazer with a nice top or shirt, a scarf, and a dark jean. As a size 14 myself, I’d say go with a trouser-cut jean in a dark wash (Talbot’s does a great one)– it’s a flattering cut that gives the impression of a dressier look. I agree with the no-cardigan advice; a structured jacket will work much better. As for the shoe, I vote for heels over flats or Chucks. The key is to find something in which you still feel like you, just turned up a couple of notches. Knock ’em dead and have fun!

  15. This happens to me all the time (I am a CPA and I have clients who have casual offices), and I always wear dark trouser jeans (I love the new flared silhouette), a shell with a blazer over it and pointy toed pumps. It’s kind of my power casual outfit. I feel like I didn’t try too hard, but I am really put together. The blazer is key, and so are the pumps. Buy the best quality and use them forever. I love the same look with sneakers in my office when I am not meeting with clients, but I feel the sneakers just don’t give you the same confidence.

  16. The last few times I’ve been stumped on a professional dress code I’ve worn a wrap dress and blazer. If it turns out to be casual, I take off the blazer and it looks like I just decided to wear a dress that day. If it’s more formal, I keep the blazer on and I look professional but feminine. I’m about your size, OP, and wrap dresses are comfortable and flattering on me.

  17. I used to work in the Silicon Valley, and know how casual it can be day-to-day. But the board is likely to be in suits, or at least wearing blazers, so you will want to wear a jacket, too. I like either option, though would lean towards a dark trouser jean, shell or button-down and a good blazer. If you present, you definitely want that blazer as it will let you take command of the room more easily. Good luck!!

  18. I’m an engineer in the Midwest, so especially on Fridays, this can mean casual, but it is also conservative (not fashion-forward). My casual Friday uniform, especially when I have important meetings, is a button-down, sweater, and sleek jeans. Any toppings (sweater, accessories) should help to make the outfit more or less casual, depending on what I need for any given meeting.

    I’m in the anti-dress camp here. If I’m in a meeting with a lot of women, it’s not a problem, but most days, women who wear dresses stick out like a sore thumb. Generally, they are interns who haven’t gotten the memo yet.

  19. Oh boy. It really depends who is on your board. Peter Thiel says he discounts ANYONE who comes to him in a suit;). If your board is expecting “Silicon Valley,” and you’re a really early startup, anything but what you wear day to day risks looking really out of place. Who are your board members? Where is the startup? How old is the startup?

    I mean, I could see anything from a leather moto jacket with skinny jeans and brogues to the sheath dress everyone’s talking about – with a boxy linen blazer – to yeah, Nikes or Chucks with boyfriend jeans.

  20. I’m at a startup too (co-founder, actually). My go-to’s in this scenario is:

    1) olive shirt-dress (tailored to fit like it’s a designer dress, even though it’s just a Target shirt dress), black leggings, black ankle boots. Pebble watch. USB chain necklace.

    2) startup/tech-themed t-shirt, lululemon jacket, ‘nice’ jeans or slacks, boots. Pebble watch. USB chain necklace.

    These choices are really all about identity politics. You want to still *look like* someone who works at a startup (pragmatic, comfortable, doesn’t spend too much time on appearances), but also express that you are “of a tribe” with the other people you’re meeting with.

    I’ve been lurking/reading for a long while, and this is the first time that casual startup dress code (my relevant environment) has ever been brought up. This makes me so happy.

    As a point of comparison, at the startup where I worked for 2 years before leaving to found my own, the founders (guys) would dress the same way for board meetings as they usually did: hoodies, tech t-shirt, jeans, sneakers. I also find that when I dress this way (hoodies + jeans, no makeup, glasses), people are less likely to question my competence, compared to wearing anything obviously feminine or formal.

    • Also, never, ever skinny heels (unless your startup is fashion-tech or subscription-services for make-up or something).

      Heels are ok if you need the height boost to see eye-to-eye with the other the people in the meeting, and if it makes you feel more powerful. But very obviously feminine ‘fashion’ choices can hurt your prospects in tech (especially if you’re making a first impression), and this includes wearing skinny heels, as opposed to something that’s more styled like combat boots that happens to give you some height.

      Relevant: https://medium.com/@sailorhg/coding-like-a-girl-595b90791cce

  21. MissDisplaced :

    Mmmm… this is a hard one. I would lean towards causal black ankle pants and relaxed but tailored blazer and low black heels or a very dark wash denim trouser jean and dark blazer. The photos shown are nice business or Friday casual outfits, but to me NOT good for a board meeting, even if it is a casual one.

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