When “Conservative” Doesn’t Feel Right

Overdressed, originally uploaded to Flickr by Sarah Ross photography.When do you break the “always dress conservatively at first” rule? Reader S wonders:

I just returned from an interview that I had yesterday at a large law firm. I knew I would be interviewing with a single partner who had all the power and authority to hire me. I had a heads up from an associate in her department that she always looked as if she walked out of a Neiman’s catalog, and I seriously considered spicing up my conservative gray suit (dress/jacket combo) with either a snazzy necklace or not-quite-so-boring shoes. But I always believe that it’s best to err on the side of conservatism in an interview, and so I nixed this inclination and slipped on my 1.75 inch black, round toe pumps and a strand of pearls. I regretted the decision the entire interview — I felt frumpy and boring. Feeling like I am perfectly dressed for an occasion always gives me confidence, and the opposite is also true if I feel that I missed the boat. I’d really enjoy a post about being interview appropriate, and still being yourself. It seems to me, that as younger, more fashionable women are taking on large roles at firms, the age-old advice of playing it ultra-safe in interviews may need to be loosened up a bit. Any tips on being polished, professional, but also stylish in an interview? I figure I’m not the only one struggling with this…

I’m sorry you felt like that! I have a few thoughts on why you may not have been overly conservative, and what you can do the next time.  (Pictured: Overdressed, originally uploaded to Flickr by Sarah Ross photography.)

Research, research, research. Here you knew that the scuttlebutt on the partner was that she always looked fashionable on a day-to-day basis — but what was she wearing in the photograph on the firm website? What does she wear to introduce herself to clients, or to appear in court? My guess is that she skews more conservative there, and those are closer comparisons to your situation — and if she were going to judge you, she would do so by comparing how she would have dressed in an interview. That said…

Always stay true to yourself — don’t ever feel like you’re wearing a costume. I have conservative outfits, I have casual outfits, and I have my “I’m meeting up with fashion blogger friends so I’d better look fashionable” outfits — but all of the pieces are things that I love. That’s not really the vibe that I’m getting from your email when you describe your pearls and your round-toe, low pumps. There are great-looking conservative items out there — classic suits, comfortable but gorgeous pumps, and interesting, detailed jewelry, all of which read conservative. Would I wear my neon pink double bib Kate Spade necklace to an interview? Probably not. But I would consider a statement necklace with a fun color, like this one, or even go for a more inexpensive, fashion-y pearl necklace (like this one) if I didn’t feel comfortable in my 16″ 7MM pearls.  The trick is finding the “conservative for you” outfit that you feel great in, but still “reads” as conservative and situation-appropriate.

Whatever happens, though, do your best to put your clothes out of your mind. I know it’s hard — I’ve been in situations where I felt under- or over-dressed, and every time I get distracted, defensive, and I start kicking myself for second-guessing my clothes. Smile, own the decision you made, and move on. (I’ve heard it sometimes helps to wash your hands after a big decision, to mentally be done with it — I’d try that here, too.)

Readers, what do you do when you show up somewhere and feel over- or under-dressed? How do you avoid that?


  1. LeChouette :

    I realize this might be a shot in the dark, but I am having a slow day at work and accordingly am doing some “what about my future?” research.

    does anyone here work (or know someone who works) as an AUSA in the greater NYC environs?

    I was recently advised I need to “know someone” (i.e. have clerked for a recent AUSA otherwise be very well connected) to get hired. True or false?

    • Anonymous :

      I’ve heard the same thing, though they often hire people who have clerked in the SDNY/EDNY and 2d Cir.

    • Don’t know about NYC, but in California, it is helpful to know someone in the office. They can let you know when a spot is coming open, if they are looking for particular experience to fill a particular unit, etc.

      If you don’t have any contacts via an internship, consider joining the federal bar association in your area and/or go to events and receptions sponsored by the court (e.g., swearing in of new judges, etc.). This can often be a good way to meet someone in the US Atty’s office. I agree that clerking in the district or circuit the office is located in can also give you a real leg up.

      • One good way of getting a foot into a USAO is to work as a Special Assistant U.S. Attorney–that is, for no pay. I know several people who saved up their firm money for a few years so they could put in a year or so as SAUSAs. Then when an opening came up, they got it.

        • LeChouette :

          Thanks very much everybody!

        • Not all SAUSA positions are unpaid. Sometimes there is a state or different federal agency paying the salary. It is definitely a good way to get your foot in the door. Good luck!

  2. For interviews, first off I’d make sure that everything fits great and is clean. If it fits fabulously, you are already on the road to not feeling so frumpy. And while I own all of those clothes you mentioned and tend to err on the side of conservatism, I try to pick one piece per interview that is not quite so conservative [though I second Kat, to leave the neon bib at home]. If you pick a little bit of a more showy necklace, but everything else is sensible – pumps, white/blue button down, classic suit, hose, conservative handbag – I don’t think anybody would accuse you of being a trend monger. For my part that was always the shirt color. I am very pale, used to have uneven skin and light hair so white (oh back in the day) and light blue would wash me out – not to mention make me feel like cater waiter. I would wear a dark suit, sensible pumps, pearl studs and a classic button down, but the button down would be in a deep jewel tone (dark, dark red or navy). It’s okay to be memorable – as long as your neon necklace doesn’t imprint on the interviewers irises to the point where they can’t remember anything else about you.

  3. I think this also depends on your field. I’m in marketing, so I would feel pretty out of place in a really buttoned-up suit with conservative jewelry. I have a black pantsuit that I wore for interviews fresh out of college, but even then, I paired it with a bright shirt underneath the jacket, and I left my hair in its naturally curly state, instead of straightening it. For daily work outfits, I have several bright colors and statement necklaces, even though I’d describe my style as toned down or conservative. Do I look more fashionable than the accountants? Definitely! Could I pass for the crazy “business attire” they showcase in magazines? Definitely not. I think it’s a fine line between appropriate with a little flare vs. unprofessional.

  4. mintberrycrunch :

    Somewhat related TJ: J. Crew skirt suit in heather flannel – appropriate for interviews (2L OCI and hopefully call backs if it matters)? I love the way mine fits, and prefer it to my black skirt suit (from BR), but I’ve always heard darker is better. Thoughts?

    • mintberrycrunch :

      This is the color: http://www.jcrew.com/womens_category/suiting/super120s/PRDOVR~23346/23346.jsp

    • Perfectly appropriate. But that with that horribly shlumpy blouse the model has on in the picture!

      • Honey Pillows :

        The chambray? Admittedly, it’s one of the ridiculous trends this season, but I kind of love it. My blue collar background coming out?

      • Too sloppy and casual for an interview. It reads “throw it on over a bathing suit in the evening after a long day on the beach” to me, not “I’m ready to be a high-powered professional.”

      • mintberrycrunch :

        Yes, definitely included the link just to show the color of the suit :) Although I do love a good chambray on the weekends. Thanks for the feedback, GW!

        • Senior Attorney :

          I love chambray on the weekends, too, and I think the model looks kinda cute. But “no denim or chambray in the office” is one of my (very very) few ironclad workwear rules.

    • Of Counsel :

      I recently bought two of those suits, one in black super 120 wool, the other in black wool crêpe. I asked J. Crew online for help with the sizing of the Petite-size skirts. It was bad advice. I exchanged one skirt for another size, and kept the other because I needed a suit to wear. Ended up spending $50 on alterations for both skirts. They will never fit well.

      The jackets fit well, except for an unfortunate, duck-ass effect caused by the center vent.

      They are very well made, with nice menswear details such as surgeon’s cuffs, that I’ve never seen on a woman’s jacket of that price.

      But if I hadn’t thought I needed the suits, I’d have returned them both.

  5. kerrycontrary :

    I’m a corporate librarian, but I was interviewing for many different positions in my field. I always erred on the side of conservative, but since I look fantastic in my suit (not to sound cocky but I do), I always felt powerful going into an interview. I’ve heard many people like to wear one piece of unique jewelry or be a little adventurous with your handbag. I always stick to a classic black Coach handbag (not one that is all labels) for interviews, but I’ve heard other people have fun with theirs.

  6. Even for a big law firm, conservative need not equal frumpy. I do a lot of interviews, and I always mentally applaud any woman who wears something other than the usual uniform of black/navy/dark gray suit and plain blouse. Someone who presents as fashion forward, yet still appropriate to the big firm environment, will almost certainly strike me as confident, which is important. I’m not looking to hire wallflowers, and black 1.75 inch round toe pumps says “wallflower.”

    • Honey Pillows :

      I love my black 1.75 inch round toe pumps!

      That said, they’re stupidly comfortable, and crocodile embossed texture.

      I think I work them pretty well.

      • I always feel like shoes shouldn’t be conservative color, style, height, and fabric/texture all at once. You need one piece of interest in the shoe. Low black heel is fine, if it’s got an embellishment or hardware, or is some interesting texture, like crocodile. If the heel is a little higher or thinner, then basic black doesn’t look so frumpy.

      • Me, too!

      • What a GREAT reply! You go girl!

    • Diana Barry :


    • My neighbor, who use to be an attorney recruiter for a big DC firm, saw me on my way out the door for an interview once and once I told her where I was headed, she said “It’s so great that you’re confident enough not to wear the same black suit/white shirt combo everyone else does. I’ve seen enough of that.” The only difference was that my shirt was purple (still a black suit), but I guess it was enough to make a difference to her. So I think she would second this.

  7. I second the comment re industry. I think it’s more about industry than interviewer. And then more about a specific office than a specific person. If you were dressed appropriately for your industry, you were probably fine. If the specific office was known for being slightly more or less conservative than the industry generally, she might have liked to see that, to see you’ll be a good fit. But even an all-powerful partner typically doesn’t expect everyone to look just like her.

  8. as someone who is on the interviewer end of this situation, i actually think the interviewee, despite her discomfort, called this one right. her style of interview dress would have let me know she was professional, interested, and “got” the rules. i’m not looking for style when i interview someone (*sigh*), i’m looking for substance and some indication that they know how to get things done.

    • momentsofabsurdity :

      For whatever it’s worth, I still don’t see why one can’t have both, and why both can’t be presented at an interview.

      • Of Counsel :

        It’s hard to anticipate your interviewer’s taste. Interviewing is hard enough. The time to explore one’s taste is after one gets the job.

        I have certain built-in style “idiosyncracies,” like curly hair and a refusal to wear high heels.

    • Of Counsel :

      I’m with you. If you’re the “guest,” it never hurts to be formally dressed. Besides, some people can’t look stylish if it killed them. What matters is that they made an effort to look presentable within the guidelines of that injury and, most important are:

      appear reasonable to work with.

      I’m not saying that looks are irrelevant in every instance, but there’s far too much obsessing about these matters.

      • Of Counsel :

        I meant “industry,” not “injury.” I think my text extender was responsible for that mistake.

    • karenpadi :

      As some who also interviews people, I second Joyce and Of Counsel.

      It is nice when someone isn’t wearing the uniform and can pull it off. Most people who try can’t. If someone shows up in a uniform, I know they can at least “act normal” and play by the rules (which is important in Law).

      • I’m one of those people that can’t pull it off, and I think it’s more of a confidence issue than a body or style issue. My sister looks amazing in what I would consider to be alternative business wear, but I just look silly. She’s still in undergrad, but wore a dusty rose pencil skirt, frilly black top, and white blazer to attend a conference, and looked incredibly professional and fashionable. However, at interview time, even she dons a plain grey dress, plain black pumps, and more subtle jewelry (the girl’s been known to wear a peacock ring with plumage that extends over 4 fingers or a full-feathered necklace, so subtle is not a word that applies to her very often!)

      • I’m one of those people that can’t pull it off, and I think it’s more of a confidence issue than a body or style issue. My sister looks amazing in what I would consider to be alternative business wear, but I just look silly. She’s still in undergrad, but wore a dusty rose pencil skirt, frilly black top, and white blazer to attend a conference, and looked incredibly professional and fashionable. However, at interview time, even she dons a plain grey dress, plain black pumps, and more subtle jewelry (the girl’s been known to wear a peac*ck ring with plumage that extends over 4 fingers or a full-feathered necklace, so subtle is not a word that applies to her very often!)

        Ugh, moderation for the name of the bird above, sorry if this double-posts!

        • If you know it’s moderation, why double-post? There’s almost never a real emergency to a moderated post..

  9. It is impossible to hit it just right with interview clothes. Once I interviewed on a hot July day in Boston wearing a nice light green cotton skirt suit with a belt. Tailored, V-neck, the right shoes and jewelry. I felt perfect. Afterwards, a female partner there said, “I don’t like what you wore for your interview – you need to jazz up your wardrobe”. But I got the job!

    • Diana Barry :

      What an odd thing for her to say *at the interview*! Which firm was it? ;)

    • Did she really tell you to jazz it up? If she’d had some sort of remark about it being green and suggesting something more traditional, I’d almost understand – but “jazz up” sounds to me like she wanted something LESS traditional! Odd.

  10. Diana Barry :

    Agreed – feeling like yourself is very important. I never wear button-downs to interviews bc I Just. Don’t. Like. Them. I like color – for an under-suit top I usually wear hot pink or red or orange, or a print, nice memorable color. :)

  11. I’m a pretty non-uniform dresser – I wear colors, accessories and my curly hair down even at interviews – but I’d never ding anyone who showed up in the “interview uniform.” I realize there are some arbitrary interviewers out there who are just looking for an excuse to ding you, but as far as I’m concerned if you show up looking relatively generic at least you’re demonstrating that you know how to dress properly. So long as you’re dressed properly, your choice of attire does not in any way affect your qualifications for a job in my office.

    • This, re: looking for any excuse to ding you in the interview! Particularly in marketing, where the job description says they want someone, “creative, fun, and passionate” that can also, “deal with vendors, internal resources, and press in a professional, straight-forward manner”, how are you supposed to know how to dress for the interview? I try to walk the fine line, as I mentioned above, with the conservative suit+colorful blouse, and let the work samples showcase the passion and creativity. It’s always awkward when you’re in a suit, and the rest of the company is in jeans! I’m of the mentality that it’s much more difficult to get someone to dress professionally vs. fun, so I’d err on the side of being conservative and letting the more fashion-forward items come out after you start working at the company.

    • anon for this :

      Ditto. I was typing up a response and you nailed what I was trying to say.

  12. How do you feel about sling back pumps with a pant suit for interviews? This is for an in-house counsel position in California (biotech).

    • Senior Attorney :

      I just want to know how you keep the bottoms of your pants from getting caught between the heel of your foot and the heel of your shoe. I love the look of sling backs with pants but this is an issue for me.

      • ditto.

      • I wear slimgbacks frequently and I don’t know what causes this problem. I have one pair of pants that “get caught” but others don’t. Is it something about the drape of the fabric? Or maybe the cut…I tend to wear legs that are cut on the narrow side, not too much flare…

  13. I almost got caught by a good-intentioned HR rep. She calls me to schedule an interview with the GC, then specifically emails me to tell me that the office is “business casusal.” Well, there was no way I was going to meet the GC in business casual. I did some research (as Kat suggested) and found out that he offices in another state, so I REALLY wasn’t going to dress-down. I wore my traditional/conservative interview suit and, of course, the GC was in a suit. I think the interview went well and I’m so glad I went with my gut.

  14. I think conservative dress is the only way to go on a big law interview, notwithstanding what the hiring partner may be known for wearing. You never know who you will meet in the hallway or if another (more conservative) partner (with influence over the hiring partner) would like to have an impromptu interview with you, as was the case when I interviewed with my firm. If you’re feeling drab in a black/navy/charcoal suit with white oxford shirt and must show a hint of your style/personality, trade in the pearls for a bold necklace or a fun (closed toe) patterned shoe, though I would probably limit your nonconservative accessory to either a necklace or shoes, not both.

    • BigLaw Refugee :

      I once showed up at an interview for a summer associate position in a small Silicon Valley (i.e., typically more casual dress) office of a San Francisco law firm wearing the stuffiest interview outfit imaginable – white silk blouse, charcoal grey skirt suit, boring shoes. I interviewed with just one partner, who was wearing running shorts and a T-shirt. I felt very awkward when the interview started, but then forgot about it and got the job.

      I have also done lots of interviewing of others, and I think either the conservative outfit the OP wore or a slightly more jazzed up outfit would be fine. I agree with others who say don’t worry about it so much, and with Kat who says once you decide, be done with it and don’t let it distract you from the substance of the interview.

  15. Perhaps the OP is in need of a new suit. I have certain work clothes that make me feel frumpy, but mostly because they don’t fit just right or they’re showing wear. In general, a well fitting suit should project a sharp, powerful image – I can’t imagine feeling frumpy in such an outfit.

  16. I’ve had really good luck interviewing in fairly conservative/traditional suits – and then wearing interesting glasses. It’s not too much, but is memorable and shows confidence. I was hired by a multinational insurance company (not exactly trendy) while wearing my black glasses with rhinestones on the corners – and it became an easy opener when networking within the company. People would remember the glasses, compliment me on them, and I could start talking about my work. I was also known as the colorful pashmina lady, and was able to network with people working in India and China because they recognized where my shawls had come from.

  17. When I was getting ready for residency interviews after finishing medical school/grad school, I hit Ann Taylor and bought my first suits. This was like 10 years ago, and I was clueless. I got a classic, conservative dark pinstripe (pant suit) which I thought I would wear for my interviews in the more staid cities and conservative programs. And then I got a couple more interesting ones for some of the more progressive cities (in my mind….). Coming from Boston, I thought NYC and San Francisco were progressive. Fashion wise.

    So I’m in NYC at one of the major Manhattan hospitals, and they gather all the interviewees into a large conference room. At least 50 of us, getting ready for 4 or 5 interviews a piece, are seated and waiting for the Chairman to come in for the initial remarks/orientation. I look around…. Every single person in the room is wearing a dark black or blue suit – men and women. Except me. I am wearing a deep red wool crepe sheath tailored dress with matching suit jacket, black heels.

    The Chairman walks into the room and everyone is quiet. He says…. “Good morning…..” and then he looks around the room. “Wow…. I feel like I’m at a funeral director’s convention….. but YOU…. YOU THERE!” And he points at me. And every person in the room turns to look at me……, and he says “YOU are HIRED!”

    • Great story :-).
      I once got hired because I hadn’t had time to erase the funny message on my voicemail yet. And I definitely applied for a job because the ad was like a funny personal. Still think of that job very fondly, even though the later HR person got all huffy. A sense of humor is a really big help if you’re going to be spending a lot of your life with a person. Never to be underestimated.
      I see that conformity is a huge plus in law, almost the whole point really, but in IT conformity is death. It’s OK if an applicant shows up in a suit, but it’d better not be too conservative. We don’t want wannabe managers who won’t do any work because it’s beneath them.

  18. I agree with many of the comments here, and I would add, how you carry yourself really can overcome many clothing issues. You feel sheepish or slightly dowdy in your conservative interview uniform? Try walking really straight, emanating energy even while you’re sitting, and think: “I don’t care what I’m wearing, it doesn’t define me!” Feeling dowdy can make you lose energy – don’t let it!

  19. Corset. I know, I know. My inner feminist is hello g at me too. I’m a fluffy gal. Size 20. I had bought a nude color steel boned corset for mt recent wedding. I find my self wearing it when ever I want to feel confident. Not to mention it allows me some different options clothing wise. It helps my posture and that reads well in interviews.

    • wow, that’s actually a great idea. I wore one for a role in an opera–a “singing” corset, whatever that is. Where did you buy yours?

  20. This is always scary for me. I try to research in advance for any function I might attend or job I might take. Or I ask someone. If I’m going to be interviewing with a retail chain for example, I scope out the place first as a visitor to check the dress code and make sure I’m dressed better for the interview.

  21. Christopher :

    It’d be great if someone could write an equivalent article for men. I mean, this woman is basically saying that she dislikes wearing stereo typically “conservative” clothing, e.g. Jackets, suits, long skirts, long trousers, etc. And it’s great that people acknowledge that there are some women who feel frumpy in conservative outfits, e.g. suit skirts, long trousers, etc, and would very much rather show off their figures in shimmery cocktail dresses/backless gowns/etc. I can totally identify with this lady. I myself hate wearing jackets, suits, etc, because they sort of de-accentuate my body, that I love showing off. A bespoke suit will never do as much justice to the artistic beauty of the human body, as say, a modern wedding gown, which shows off every curve and angle of the female form, as well as her arms and cleavage. You just don’t get an equivalent kind of celebration of human beauty in a suit, no matter what the fellows at GQ say. I mean to say, you can show off the human body to a CERTAIN extent in a suit (e.g. by wearing a low-cut top underneath), but that’s about as far as you can go.

    I mean – Women in suits e.g. Air stewardesses, look AMAZING, but i’m sure for many of them, their tailored suits are simply a job uniform, and nothing more, and when work is over, they will be more than happy to slip into their sleeveless blouses/slinky gowns/cocktail dresses/skinny jeans/high-slit skirts when playtime comes. That’s why men’s clothing adverts don’t make sense at all – If I’m a lawyer, and I wear a jacket and tie 5 days a week, then why would I want to spend my play time in my work uniform? SILLY!

  22. Err on the side of conservative — but in the context of your own style, confidence and comfort. Great point!! If you are betraying your own style by exchanging confidence/comfort for conservative, then don’t do it! Great advice…