What to Wear on the First Day at a Very Casual Office

Pictured: Clean slate, originally uploaded to Flickr by mikecogh. What should you wear on your first day at a very casual law office? Reader F wonders…

Thanks for the great blog – it’s been holding my hand, fashion-wise, since I started law school. I have a question: what should an articling student wear to work (especially on my first day) at an extremely casual law firm populated with some very prestigious lawyers? By “extremely casual” I mean that the last time I saw my principal at the office she was wearing ripped jeans and a vintage poncho/jacket sort of thing. She is a very senior & highly respected lawyer, and I am a lowly student, so my quandary is this: on the one hand, I don’t want to look like an overdressed nerd in a suit, but on the other hand, I clearly do not have the seniority to dress as she does. How to split the difference? What should I wear on my first day? Thanks!

Great question, F — you’re right to assume that you need to bank some credibility before you can start wearing very casual things. We’ve talked about how to have a great first day on the job, as well as what to wear for a business casual office, but we haven’t talked about what to wear at a very casual office. For my $.02, this is very field specific — and for most lawyers I’m going to fall on the “be safe and wear a suit” side of the continuum.  Your job involves representing other people, not yourself; your job requires you to get immediate respect on first impressions (e.g., from judges and juries) — and your boss wants to know that you understand that.  Since you describe this as a “very casual office,” I’m guessing the odds are approximately 90% that you’re going to immediately take off the blazer and leave it in your office — so make sure you like your outfit sans blazer — but you still want to show up and have that “I’m here and ready to work!” conversation in your suit. (You can then let your blazer live at the office to become your wear-with-everything black blazer.)  

The real question, in my mind, is what to wear the second and third day on the job, when people will expect you to be a bit less formal (unless you know you have something big coming up). For planning purposes, I’d stick with very conservative, classic pieces (knee-length dresses with sleeves and high necklines, full length trousers, button-front blouses, blazers), but start to have some fun/show some personality with your shoes, jewelry, and how you wear the pieces (e.g., fun with layering, scrunched up sleeves on blazers and blouses, etc).

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Readers, what would you advice a lawyer to wear on her first day on the job at a very casual office?  For those of you in professions where “suit=nerd,” what would you tell Reader F to wear?

Pictured: Clean slate, originally uploaded to Flickr by mikecogh.

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  1. I think casual is the order of the day. Women should not have to dress formally in order to be taken seriously. Witness Sheryl Sandburg.

  2. I work in a very casual law office. No one, not even the students, are expected to wear a suit unless they are going to court. If a student or new lawyer were to show up in a suit when it wasn’t required, they would be told to come back the next day dressed more appropriately.

    If your office is anything like mine, I’d split the difference by wearing a skirt or nice pants (though not necessarily wool; cotton is fine), and a button up top. Once you’ve been there a while, you can mix in jeans.

    • I agree. I think wearing a suit would be overkill.

    • agree w/all the “don’t wear a suit!”s

    • Same here – no suit! I also work at a very casual office and on my first day I wore dark wash skinny jeans tucked into Frye boots, a Theory blazer and an accent scarf. I felt fine. I only wear suits if I am meeting a client or going to court. Did I mention I love my job?

  3. I am a lawyer in a very casual office and I cannot disagree more with the “wear a suit” advice. I don’t work at a law firm, but even so, in a casual office the suit will come off as stuffy, awkward and out of place. On the rare occasion suits are worn in my office that’s how it feels. However, I often wear blazers (as I’m young but senior in my office) to add gravitas/cache (to my jeans & t-shirts). I recommend that for a very casual office start with dress pants/skirt and blouse and blazer (or some combination thereof). Not a formal suit. Wear some more interesting shoes or jewelry than you might wear in a more conservative office. By being dressy business casual in a business office you can exude experience without making people uncomfortable with the clearly way-too-overdressed look of a suit.

    • AGREED. I have now worked for two very casual law offices.

      Don’t wear a suit. Really, just don’t. I think a blazer with a pencil skirt is fine, but a full on suit will be overkill.

      For a first few days, I’d stay away from denim, then stick with dressy denim only. I’ve got a dark wash pencil skirt and some trouser jeans in regular rotation. I don’t wear skinny jeans or jeans with lighter washes. I *might* get a pair of white jeans this summer, but only because I’ve been here long enough. I don’t know if I’d do it as a summer associate though I would consider a white or colored denim skirt in an appropriate length OK. Maybe this is a weird double standard. Not sure.

      I think the trick to looking professional in a casual setting is to mix casual piece + dressier piece + statement accessory/shoe. Ballet flats in bright color + wool pencil skirt + cute structured shirt is usually a good bet. Denim + blazer + statement necklace. etc. (I find LOFT to be really good for casual blazers)

      Find casual clothes with some structure. T-shirts with some spandex in them and nice sturdy hemlines, etc.

      And while all clothing should be in good condition, that manta is especially true for casual wear. When the t-shirt starts to lose its shape from too many washes, it’s time to take it out of the work rotation.

      • In-House Optimist :

        Suzy, are we the same person? No suits, no suits! My office is super casual (it often upsets me that people are this casual. There’s casual, and then there’s sloppy. My company tends to be on the sloppy end of the spectrum.) and I’m often the most dressed-up person here. I’m also the only attorney. My first day I wore a cute dress with a blazer and flats and it worked perfectly. Typically, I just make sure my casual outfits are pulled together (accessories and fun shoes are my friend, along with casual blazers … though as I type this I’m wearing shorts, flip-flops and a t-shirt). Anytime I wear a suit, everyone asks me if I’m going to court or “if I’m firing someone.” Not sure why I’d wear a suit to fire someone, but it definitely sticks out and makes people nervous.

        • Midwest GC :

          Completely agree with In-House Optimist. Suits make people very uncomfortable at super casual offices. I am GC at a manufacturing company (and young for the position). I have to balance being too underdressed with being too stuffy at the office. Into almost my fourth year in this position, I now wear pretty much whatever I want to the office (including the dreaded flip-flops!), and if I dress up much at all I definitely get the side-eye. Any time I wear a suit, I’m asked if we’re about to get some sort of federal inspection or if someone important is coming to the office that they need to be aware of.

  4. I disagree with Kat’s advice. This does not sound like the kind of office where you should wear a suit, even for the first day. A nice pair of slacks or a pencil skirt with a blouse or button-front shirt, and maybe a pop of fun jewelry, would be a better choice in my opinion. That would show that you know how to dress professionally but are not completely tone-deaf to the office culture (which is how it sounds like you would look if you wore a suit).

  5. momentsofabsurdity :

    While I understand the standard advice on this site that you can’t be penalized for being overdressed, just underdressed, I honestly don’t think that’s the case. I’ve worked in places where if you showed up in a suit on your first day, it would mean you really didn’t pay attention to any contextual cues from your interview experience, might send off the vibe that you are too buttoned up or stuffy, would suggest you didn’t do your homework on our company, and would just generally present you as a fish out of water with relation to our company culture. Your first day you’ll meet a lot of new people, and that’s not really the impression you want them to have.

    I would just send an email before your start date saying, “Hi Hiring Manager, since my start date is coming up, could you please let me know if there are any dress code norms I should be aware of?” and then dress one notch above that. That may mean as casually dressed as “chinos, flats and a wool sweater” in a shorts-and-tanks environment.

    • TO Lawyer :

      Yes I would do exactly this.

      Also have fun with your outfits! You can dress professionally still but perhaps a bit more bold. I see lots of interesting colours and patterns in your future! I would also second the recommendation of blazers in interesting textures/patterns/colours. You can look professional but still appropriate for your office in a fun blazer!

  6. I agree with the comments so far. I wore a pencil skirt, knit top and cardigan to my first day summering at a casual non profit and dialed it way down from there.

  7. I’m not in a “suit=nerd” office/field, but more the “suit=overdressed/do you have a job interview somehwere else later?” type situation. I wore a suit to my interviews, but haven’t since.

    My “go-to” is wrap dresses, and I feel like in a more casual office you can go bolder with the prints too. I try to get 3/4 sleeve ones because they transition nicely into fall, and my more neutral ones I wear through the winter with tights/boots.

    Other than that, I wear a lot of blazers (structured, cropped, ponte knit, etc) with nicer blouses underneath. For bottoms I generally wear pencil skirts or fuller trousers. Summer gets even more casual here, so sometimes I’ll wear colored pants or slim-fitting capris.

  8. I’m not a lawyer, but in my first day in a major corporation with “business casual” dress, I wore a blazer with a very muted floral skirt. It didn’t seem inappropriate at all. A suit probably would have been ok too, but that would have been the first and last time. Also, I asked the hiring manager about appropriate dress when I accepted the offer, and she wasn’t at all annoyed and explained the casual dress code.

  9. CasualCanadianLawyer :

    F, I think you are worrying too much about being “an overdressed nerd in a suit” on your first day – suits are part of a lawyer’s wardrobe, and no other lawyer will ever think you are overdressed if you are wearing one in an office. I speak from experience on this one, because I am a young lawyer who works in a very casual office – casual enough that one of the partners wears shorts and skate shoes every day, unless he is in court. Most days, the other lawyers’ clothes range from jeans and a t-shirt to business casual. But some days one (or more) of the lawyers wears more typical business clothes and they certainly are not judged for it.

    So, I agree with Kat that you should show up on day 1 in a suit, but expect to take the jacket off. I also agree that, at least at first, you probably will not want to wear torn jeans or a poncho. For the rest of your articles I’d say that separates and cardigans will be your best bet. As you settle into the office and get to know the culture you can mix them around to be more or less formal.

    One other thing I learned when I moved to a casual office from a big firm – depending on who your clients are, meetings with them may actually call for less formal clothes. My firm’s clients are typically regular people who feel more comfortable with me when I am not in a suit. So, if anything, I tend to dress down a bit on days I am meeting with clients.

  10. Katherine :

    I’d do a grey non-wool suit with a colored t-shirt underneath, and bring a scarf to put on with the t-shirt once the jacket came off. Or, you could bring the jacket and not necessarily put it on at all.

  11. Veronique :

    I swear by three piece dressing in my business casual office: slacks/skirt with a shell/blouse (usually not button-up) and blazer/cardigan. I usually wear a blazer or cardi with dresses, but sometimes wear them on their own if they have sleeves. I would wear one of those combinations for the first day (leaning towards a blazer rather than a cardi). Color and pattern also add a more casual feel to classic shapes. Above all, ensure that everything is in good condition (no rips for you!) and fits well (not too tight, short, etc).

  12. I work in a very casual office (I’m in finance, not law, FWIW), and our firm takes pride in it as part of our company culture. I’d recommend following the dress code for your first day. If it’s casual, be casual (yet polished). I wore dark denim jeans, a silk blouse, and pumps, and I honestly haven’t veered much from that uniform since I’ve been here. No one here expects people to show up in a suit just because it’s their first.

  13. I agree- I think a suit might still be too stuffy. I’d wear a conservative boat-neck, 3/4 sleeve, knee length ponte knit dress in a traditional color with a statement necklace and professional wedge heels or pointy flats. This way, it could skew either formal professional or less so, depending on what everyone else is wearing.

  14. And you know, since not everyone in the world is a lawyer, make sure to ASK what proper attire is for the office. In my field (engineering), the wrong shoes can mean hanging out in the office doing nothing instead of tagging along and observing cool projects. Not every manager is going to think to inform an intern or new employee ahead of time.

    • At my office we have causual ONLEY in the Summer, and onley on Friday’s b/c the manageing partner does NOT like to go all the way to the HAMTONS on the train weareing a SUIT. Instead, he wear’s Kacki’s or jean’s and a POLO shirt. We can wear anything we want and that is great b/c it is very hot in the City on Friday’s especially if I am walkeing to Macy’s across town.

      Haveing said that, you should alway’s ask before dressing down. We already have esablished our repueatation’s so how we dress is secondeary. As a new lawyer, you have to dress well, at least until your repueation’s are established. YAY!!!

  15. Where is this casual office? I work (as an in house lawyer) for an entertainment company in LA and nobody ever, ever wears a suit (except our general counsel when he very occasionally has to go to a deposition). And the women NEVER wear suits.
    1st day: Sheath Dress with a contrasting blazer. After that, take a cue from what other junior people are wearing.

    I think if you’re uncertain, dresses with cardigans and flats are almost always appropriate. But my guess is jeans and a blazer will also be appropriate. My real rule is to never wear anything that you’d wear to work out, or anything you can’t wear a real bra with.

  16. I agree that a suit is overkill. It’s probably not going to hurt you, per se, but will probably look tone deaf (and depending on office culture, might open you up to some ribbing for the rest of the summer, which is what happened at one place I interned). This is especially true if you’re on the West Coast, I think, and as a Pacific Northwesterner now living in D.C., I wouldn’t even consider wearing a suit if you’re in, say, Portland.

  17. I definitely would NOT wear a suit to the office on your first day. If ripped jeans are the norm, a dress or skirt will already be plenty dressy.

    I’d opt for a more casual pencil skirt (one with a print, but nice—not jersey—material) and a more casual button down, like in a cotton or even chambray. The skirt and button down will keep it a little dressier, but the prints/fabrics will balance it out with casual. And I’d wear some nice flats, not heels with this combo.

    Or you could opt for a tailored, cropped pant (like a J.Crew cafe capri) and either a button down or a nice blouse. That is dressy enough.

    I guess I’d wear something that I’d wear to a fancy brunch. If that makes any sense.

    • I’m thinking this is a good occasion for one of those brightly-colored Target skirts that were discussed here at length a few months back. Also good for an intern budget.

  18. Olivia Pope :

    I agree with the commenters that this would be the rare exception to the “suit on first day” rule. I friend of mine did a “pencil skirt + nice top + cardigan” combination and all the other attorneys asked her why she looked so nice.

    This reminds me of my first casual Friday when I was a summer associate at my business casual law firm. I followed the advice of The Hive: trouser-cut denim, silk shell, and cardigan. A partner thought no one had told me about casual Friday! I wore skinny jeans, shells, and “interesting” blazers the rest of the summer.

  19. Yes, this advice seems off to me. Maybe I’m old and feel like I’ve earned my stripes, but suits on the first day on the job don’t get worn by me, ever, including at Big Law. I earned the right to be here. Be impressed by me. I’m the suit, the suit don’t wear me. #Swagger

    • I work in investor relations in biotech, and my go-to first day outfit is a sheath dress, cardigan and interesting necklace. In my company, maybe even my whole industry, a suit on day 1 would look like you were trying way too hard, to the point of obnoxious.

    • THIS!!! I love this comment most of all!

      I agree with the comments so far that this is not a suit on the first day scenario. Knowing your company culture is important. I would think it was odd, if an intern came in wearing a suit to my business casual, casual on Fridays restaurant company office. I am General Counsel, and I only wear suits for Board Meetings, and the rare occasions I have to go to Court. Even then, I am the most formally dressed in the meetings – purposeful, since I am junior to the rest of the executive team by 25 years and the only woman.

      I say a dress with blazer or skirt/slacks and blouse is fine for your first day. It’s more about how your outfit comes together and making sure you are still “well-groomed,” even when casual. I am sure you will be in jeans and blouses, sometimes with sometimes without blazers pretty quickly though.

      Good luck!

  20. I work in a very casual office — as in, I’m wearing jeans and sandals as I type this. I could show up in a suit without ridicule, but everyone would assume that I had a Very Serious Meeting. So if your office is similar, I’d err on the side of business casual. On my first day, I wore black dress pants and this copper-colored button-down. Nice enough to be safe, casual enough not to stand out.