How to tell a new employee her clothes are too sloppy?
January 17, 2007 11:36 AM   Subscribe

How do I gently inform a new employee that she needs to dress better?

We recently hired a new part time person for our (very) small staff. She's wonderful; we love her; she's already great - work-wise. Appearance-wise, however, she leaves something to be desired. She's sloppy; her clothes don't fit well or match and they're just inappropriate for her position, which is very much in the public eye. She's also in her mid thirties, so you would think that she would know dressing like a college student is no longer appropriate. Her clothing style is what we here in Asheville call "crunchy" btw: messed up old Ugg boots, corduroy jeans that don't fit, a not quite clean shirt that clashes horribly with the much too small cardigan over it, striped kneesocks with a plaid skirt and so on. We do have a dress code but it doesn't cover this kind of thing: it just says no jeans & no logo T-shirts & please be neat.

She doesn't have to get all corporated out - noone expects her to wear a suit every day or anything - but she should look like an adult, have clothes that are basically business to business casual and are clean, match and fit. This whole thing is hard for me because I certainly don't dress like a corporate clone: I mostly just wear black and try to make sure that everything looks at least kind of "officey." So I have no idea how to approach this entire conversation and, as I hate confronting people for anything at all, much less something personal like this, I am turning to the hive mind.
posted by mygothlaundry to Clothing, Beauty, & Fashion (60 answers total) 4 users marked this as a favorite
What Not To Wear. But seriously - maybe she can't afford new clothes. I worked a job where they paid me barely minimum wage and expected mr to wear business suits and all that. I could barely afford the ramen I was eating for breakfast, lunch and dinner. Maybe try to find out why she wears the clothes she does - is it a matter of money or simple laziness, or lack of style? Be her friend, take her out shopping and steer her to the business casual racks.
posted by Sassyfras at 11:43 AM on January 17, 2007

Best answer: Hmmm. But based on your description of the dress code - she isn't fulfilling it. For example: Her appearance is not 'neat', especially not with messed-up Uggs. I think that you just need to be upfront with her. Pull her aside, mention what you've said here, that her work is great etc. Then mention that there is a dress code, and that she is in the public eye, and she needs to look more in line with the office environment.

Is there some other issue, like money? Can she afford better and better-fitting clothes? Or has she never worked in an office before, so she doesn't know the standards? These are more difficult situations.
posted by typewriter at 11:44 AM on January 17, 2007 [1 favorite]

I guess this doesn't work too well in a very small company, but what one of my previous managers did was just send out a general email to EVERYONE reminding them of the dress code. In your case, you could say something like "I know the dresscode only addresses X and Y, but do remember you all have customer-facing roles" or something to that effect.

Hum. Other people here will probably tell you to just sit her down and talk to her.
posted by ClarissaWAM at 11:45 AM on January 17, 2007

We had this problem at my workplace as well. Rather than single her out in an "intervention" (it was a similar kind of awkward situation where a 40-something woman dealing with the public was dressing in miss-matched teeny bopper outfits), the big boss wrote up an dress code policy memo which was posted and distributed. We all had to sign a copy of it. Everyone knew what it was really about, and she did get the point.

If this were a 22 year old in her 1st job, you could offer to take her shopping for business clothes, have a sisterly talk over lunch, etc., but this woman is probably just dressing the way she's gotten away with dressing at previous jobs. She's either not picking up on the cues around her or doesn't think it matters. If she still doesn't "get it" after an official policy is set and publicized, then you can do a one-on-one intervention.
posted by availablelight at 11:47 AM on January 17, 2007 [1 favorite]

Did she wear business casual to the interview? If so, then I think you can paint it as a misunderstanding -- that the office expects similar attire every day.

I think it's harder to assess standards of clothing in a small office because it seems more idiosychronatic than standard (not a big enough sample size). So perhaps the dress code needs to be made more specific.
posted by xo at 11:48 AM on January 17, 2007

I would second keeping in mind that even if she doesn't dress the way she does now because of finances, money might be an issue with her suddenly buying a lot of new wardrobe items that are more work-appropriate (especially as you mention she is a part-time employee). And I don't envy you the discussion, but it might be useful to stress that it's OK if she gradually builds up her wardrobe over several pay periods.

You might keep an eye out for sales or coupons at department stores and mention them to her in case she's looking for new items for work. But as I type that, that's pretty passive-aggressive even though you clearly mean well. It might be best just to sit down, praise her skills as a worker and politely request she wear clothes more suited to a professional environment.
posted by handful of rain at 11:48 AM on January 17, 2007

If money is the issue, or she is just entering the workforce late, maybe the company can give her a bit of money for *one* proper shirt and a pair of pants. Just to start her off....I mean, at a big discount type place, you could get something business casual for probably under $40 for a whole outfit. (Of course, it wouldn't be high quality, but a start...)
posted by typewriter at 11:52 AM on January 17, 2007

If you were the one that hired her, then I suggest you just have a sit down with her. But, you should take the blame. Say that you must not have made the dress code clear, maybe say you appreciate her style and all, but that you all need to put forth a professional front and while that does not mean suits, it does mean more traditional wear. You should communicate your approach to dressing (i.e. mostly black and officey), and honestly try to tease out whether she has that sort of clothes and/or the money to get them. If she needs help with money to get new clothes, then perhaps a stipend for $100-200 to get her a weeks worth of officey type things (easily done at a combination of Target, TJ Maxx and thrift stores).
posted by sulaine at 11:53 AM on January 17, 2007 [1 favorite]

...Places like Old Navy, Steve and Barry's, Target, TJMaxx, and even *cringe* WalMart have great (and cheap!) business casual seperates, and you can find nice looking stuff at a well-stocked Salvation Army or Goodwill as well, so it shouldn't be a cost concern.
posted by availablelight at 11:53 AM on January 17, 2007

She's also in her mid thirties, so you would think that she would know dressing like a college student is no longer appropriate.

If you have to talk to her, do not say this. The attire is only inappropriate for the customer facing side of the business. Do not condescend her personal style. You'll come across like Regina George.
posted by pieoverdone at 11:53 AM on January 17, 2007

I'll warn you that I work in a similarly small office, and if somebody at work bothered me about my clothes even though I was in compliance with the dress code, I would probably find another job.

If you want people to "look like an adult, have clothes that are basically business to business casual and are clean, match and fit", then those words or their equivalent should be in your company dress code. I really do not see any way to "gently" tell someone something like "you would think that you would know dressing like a college student is no longer appropriate"; either buck up and tell it like the boss (and don't be surprised when she tells you and your part-time job to stuff it) or live with having a colorful employee.
posted by vorfeed at 11:55 AM on January 17, 2007 [1 favorite]

Vorfeed - I am not sure that I would agree that the employee is in compliance with the dress code, based on the poster's description.

BTW - I am a fairly colourful dresser (to put it mildly). I work part-time in a tolerant office. Yet, when we have meetings, or are heading to the bank, well, I pull out the iron and sometimes even the pantyhose!
posted by typewriter at 11:59 AM on January 17, 2007

vorfeed, it's one thing to live with a colorful employee that doesn't represent your business to your customers. I could understand your point of view if you never had face-to-face contact with customers. But in this case, it sounds extremely legitimate to request that the employee have a professional appearance during work hours.
posted by knave at 12:01 PM on January 17, 2007

you can find nice looking stuff at a well-stocked Salvation Army or Goodwill as well, so it shouldn't be a cost concern.

Unless of course, she is taking the job on as a second job to make ends meet while raising her two children alone after her husband died a tragic and costly death.
posted by Sassyfras at 12:02 PM on January 17, 2007 [2 favorites]

Just chiming in re: the issue of affordable business/business-casual clothes: plenty of nice stuff is available at Target! The Isaac Mizrahi line is sometimes a little gaudy and goofy, but the basics are great -- affordable, cute, and absolutely office appropriate (I've got several pieces in my wardrobe that I wear regularly). Same with the other Target "business" brands like Merona -- tons of skirts, tops, pants, and jackets under $40 a piece, and often under $20.
posted by scody at 12:02 PM on January 17, 2007

Has she ever come in dressed appropriately -- say, for her interview? It would be less awkward if you could point to "what you wore to your interview," or "what you have on today" as being appropriate.
posted by wryly at 12:04 PM on January 17, 2007

I think most of your problem would clear up if you asked her to stick to solid colors to blend in with the rest of the staff. Her clothing seems to be important to her. Even though she may not be 'good' at dressing, she feels comfortable and likes the way 'younger' clothes make her feel. Perhaps phrase it like:

We love your vibrant individuality, but we'd like you to wear solid colors since you're making the rest of us look old and boring!

She may not think it's genuine, but it gets the point across and probably won't hurt any feelings. When she does wear something you find appropriate, compliment her. I think it's a good compromise.
posted by cowbellemoo at 12:13 PM on January 17, 2007

if she was hired with something like a 90-day probationary period perhaps you could broach this subject at her review.
posted by antitext at 12:16 PM on January 17, 2007

I would not contact her directly but instead make a general statement to the office personnel. That way you avoid singling her out and you still get the message across, and you can use it for reference later in case the discussion has to happen again.
posted by arimathea at 12:28 PM on January 17, 2007

Uh, you can't just stand there in front of ten people, and generally tell everyone that they should wear what nine people already are wearing. It's insulting, makes eleven people uncomfortable, one person embarrassed, and one person look like an inconsiderate asshole.

You're going to have to have a private conversation like other people have mentioned. Uncomfortable, yes, but that's why you're the boss/manager type making the big bucks. Because supposedly you can do these kinds of things.
posted by ctmf at 12:40 PM on January 17, 2007 [2 favorites]

"you can find nice looking stuff at a well-stocked Salvation Army or Goodwill as well, so it shouldn't be a cost concern."

Unless of course, she is taking the job on as a second job to make ends meet while raising her two children alone after her husband died a tragic and costly death.

posted by Sassyfras at 3:02 PM EST on January 17

Or she's actually living in a cardboard box and using a public washroom to give herself spongebaths because she's lost everything at the races, etc. Maybe she literally has not a dime to spare. But for $15 (American dollars!), I've walked out of the local Salvation Army with 3-5 items of near-new (sometimes with tags still attached) clothing--skirts/pants are about $3-5, shirts are $1-3, sweaters are $5, etc.

If she's that destitute, most cities also have programs for lower-income women returning the workforce that offer either a clothing voucher, or a "closet" of new or gently used professional clothing.
posted by availablelight at 12:42 PM on January 17, 2007

Be gentle and straightforward. State your specific goal and your reasoning behind it. Make it clear that this is a professional, not personal, requirement.

As a stubborn lousy dresser, I resented the hell out of a previous employer's hamhanded attempts to get me onboard the dress code with passive-aggressive hints and mimework. I've reformed a little over time, as I've found a bit of zen and flexibility in myself, but that's mostly in spite of that experience. Dressing is a personal thing, and I'm not remotely a clothes nerd. I have to imagine it's even more so for someone who is into clothes.
posted by cortex at 12:43 PM on January 17, 2007

Response by poster: Thanks, but we don't want a corporate clone, as I said above. Her outfits would be fine if they fit properly. I guess I'm not putting this very well, but without pictures, it is difficult. The overwhelming impression is of sloppiness and lack of care, not of freewheeling individuality. I don't dress corporate myself, actually, and I would never expect a part time employee to wear a suit or any such thing. I was doing her job myself just a couple of weeks ago and I dressed the same way I am right now, which is individual & fairly eccentric, but sort of more pulled together, if that makes any sense.

I am only asking that she look neat, which she does not. This is a tough call; I'm well aware of that (it's why I'm asking here) and I don't want to suppress anyone's individuality, crush their style or any such thing, but there's a fine line between making a fashion statement and looking like you're panhandling. I am also between a rock and a hard place here as I am the person who is temporarily in charge and I am the person who will get the complaints from the elderly board of trustees members and volunteers and so on. Actually, those of you who are saying she is not within the dress code are probably close and I need to rethink that - I think you're right. And the first couple days she was here she was totally fine - it just started to slip rapidly after that.
posted by mygothlaundry at 12:49 PM on January 17, 2007

This isn't a big deal -- it's only by pussyfooting around that it will seem like a personal condemnation. They way she dresses is fine, it's who she is, whatever -- it just isn't appropriate for this job, and any adult is going to be able to understand that. There's a stated dress code, and there's an unstated dress code -- she didn't pick up on it, so whoever her direct supervisor is should just point it out in a matter of fact way.
posted by Methylviolet at 12:50 PM on January 17, 2007

Can you somehow phrase it as the customers' complaining about her credibility, and your having to spend time assuring them that she's professional/knowledgeable/a grown-up? Something like, "It seems that a lot of our clients aren't really taking you seriously, and so it's creating more work for me because they're coming to me rather than asking you questions. I'm guessing it's because they're a bit put off by the way you dress; all the colors and such make you look much younger than you are. Do you think you could tone it down a bit?"

That sounds cheesy written out, I know... I'm just trying to see if there's a way to spin it as "*I* know you're competent, but you're not coming across that way to people who matter, and that's causing problems for *me*. So here's a way that I think you can fix that."
posted by occhiblu at 12:50 PM on January 17, 2007

(On non-preview: Or, "It seems our volunteers and board members aren't taking you seriously, and I'm having to spend time reassuring them that you're good at your job, etc. etc.")
posted by occhiblu at 12:52 PM on January 17, 2007

Response by poster: Also, while I don't think she's rich I don't think she's hurting that bad either, or not more than any of us who work here: this is a non profit. We are not making big bucks.
posted by mygothlaundry at 12:52 PM on January 17, 2007

Whatever you do, please do not make it some sort of "general office memo", especially since you mentioned it was a (very) small office.

Everyone will know who the memo is really directed at (including the person in question), and you'll be singling them out further and possibly embarrassing them, which is something I assume you want to avoid.

Doing things to avoid confrontation can sometimes make the situation worse -- being honest and direct is often the way to go.

If you were in her shoes, wouldn't you rather your boss/superior address you directly one-on-one with any problems they have with your work, or read about it in a memo for everyone else to see?
posted by jca at 12:52 PM on January 17, 2007

Maybe you want to say "traditional fit" or "conservative fit" instead of proper fit.
posted by Methylviolet at 12:53 PM on January 17, 2007

Years ago, a then-boss (small office) took me aside and said something about my clothing.

Which was that I didn't have to dress like I did, since people hardly ever came into the office, and if somebody was going to, they knew about it in advance. Didn't have to worry about it every morning, etc.

I was too nicely dressed for their office, more or less.

It amused me a fair bit, and was very nicely put. What's your rationale for wanting nattier attire? Use it. Had my 'problem' been the other way around, it would've been a completely reasonable request. Do customers come into the office? Even if it's rare, just note that they do, and -- well, don't make it sound like it's you that thinks striped socks with plaid skirts isn't attractive.

That sort of thing is cute at 20 and getting a bit sad at 30, I think. It also doesn't fit my definition of "neat," but, given the ambiguity, maybe consider re-writing the dress code.

Agreed re. decent work clothes can be found on the cheap. Striped knee socks are not 3-for-a-dollar white tube socks; it doesn't sound like a poverty problem.
posted by kmennie at 1:00 PM on January 17, 2007

Best answer: Did you address a dress code when interviewing and/or hiring her, or did you assume that people would, by virtue of common sense, dress as you expect for the position? (I do not mean the latter clause of that sentence sarcastically.) Was there any employee materials given at the time of hire (employee manual, etc.) which lay out the dress code — in other words, has she in any way been notified prior to this incident that there is an expected code of dress in this office, to which she then chose not to go by? Did she wear what she is currently wearing to the interview, or did she wear more formal interview clothes?

I honestly think direct one-to-one diplomatic honesty is the best policy in this situation. Ask to meet with her. I'd start by first telling her what you told us: that in nearly all ways both you and others think she is doing great, and are very pleased with her performance. If I were in your shoes, I might then segue by saying something to the effect of this: "That having been said, I do need to ask for one small tweak[insert if dress code policy has been informal/unwritten/unverbalized: ", and it's partially my fault for not communicating this properly to you when you were hired." Even if you don't really feel it's your fault.] I want you to be comfortable in your working environment, but since your position has you working so much in the public's eye, in many ways you're the face our company presents to the public. As such, I need you to dress more in a [use either the "business formal" or "business casual" buzzword here] attire, such as [here, lay out in positive statements what you desire, without critiquing her current outfit -- i.e., "skirts or pants, solid colors" -- even if she asks something like "what's wrong with what I'm wearing?", I personally would not go the criticism route]." Wrap it up with saying something like, "Are you currently set up for that?", so that if this would involve clothing purchase for her, she realizes that you realize that there might be a financial impact of this request on her. If she says she's not set up for this, then, depending on how you feel about the stipend idea earlier, address the issue as you see fit, either by outlining a stipend, asking her to buy a few pieces as she can with an overall deadline of daily wear on such-and-such-a-date, suggesting affordable local businesswear outlets, etc.

I would end the meeting by saying at the end something to the effect of: "I want you to know that I genuinely meant the praise about your performance at the beginning of this meeting; I wasn't just saying that to soften you up before bringing up the businesswear issue. We're really glad you've joined us here; Flip Burkington over in the Sprocket Maintenance department says his sprockets have never gleamed as much as they have since you've been hired. This is just a small adjustment, that's all." In that way, she's not going to think you laid down fake praise just to reduce the impact of the criticism.

I hope you're not insulted by me getting so way overspecific — but you asked for advice and that's my take on the situation! ;-)
posted by WCityMike at 1:02 PM on January 17, 2007 [5 favorites]

Be gentle and straightforward. State your specific goal and your reasoning behind it. Make it clear that this is a professional, not personal, requirement.


The best way to do this without everyone feeling bad is to treat it like the sort of transaction that is expected to happen between a manager and an employee. If she wants to excel there, she'll appreciate your candor; if her appearance is more important to her than her own and the company's perfomance, then it's best for everyone involved that she and your company part ways. But hopefully it won't come to that.

Be prepared to expect candor as well. If she wants to tell you why she dresses the way she does, listen, and see if the two of you can find a solution that meets both of your needs.

It does sound like you might benefit from a stricter formal dress code than "please be neat", though. But if so, be sure to take care of that separately from the issue with this employee, and long enough after this employee's situation is taken care of that the connection can't be made.

On preview: WCityMike's got it too!
posted by mendel at 1:05 PM on January 17, 2007

I think that you might overestimate how invested and invested in a new part-time person, being paid an average non-career office wage, might feel. Personally, if I were not making a huge sum and on top of that was getting part-time hours, I would find the notion that I need to buy new clothes over and above the dress code a little hard to swallow too. If you are going to say something make it a mass communication with specific notes like "corduroys are considered jeans" or what have you. Giving her a talking-to doesn't really seem fair to me.
posted by loiseau at 1:06 PM on January 17, 2007

With the addition of the news that she's "slipping" in her wardrobe, it's possible that she's either 1. pushing limits or 2. run out of clothing before laundry day. It sounds like you're gearing up to have a sit-down with her about the issue, but that you aren't certain what the issue is.
In your initial post, you seem unhappy with her choices in clothing (or how they fail to match?), and in your follow-up you seem only unhappy with the fit of the clothing.

Fit of garment is part and parcel in one's choice of garment. The way items and colors go together is exactly what makes a pile of clothing into an outfit.

You have a problem with the way she dresses, but you seem reluctant to accept it. Also, it's possible that when you bring it up, she'll be all "screw you, I don't need a job that tells me how to dress" and she'll quit, no matter how nicely you try to broach the subject. If that happens, you're well rid of her.
posted by Sprout the Vulgarian at 1:08 PM on January 17, 2007

I just thought I'd throw my two cents in there. If I were in her position -- dressing inappropriately for my job and perhaps not realizing it -- I certainly wouldn't want a memo to get sent out to the whole office about it! That's humiliating, and makes what should be a private employee/boss matter into office gossip.

I'd rather be taken aside (maybe not a full on "sit down" conversation, but just aside) and told that I was not doing something right, than to have the whole office made aware of it via a "public memo" that's really only addressed to me.

You're the boss -- she's your employee. Tell her what's going on, and give her an opportunity to respond and fix the problem, before you take her down a notch in front of the whole office.
posted by Kadin2048 at 1:13 PM on January 17, 2007

I don't think there is anything wrong with saying proper fit.

I also don't think there is anything wrong with taking her aside and telling her you aren't trying to stop her from expressing her personal style, but she needs to express her personal style in CLEAN, ironed, well-fitting clothing.

To me, her knee socks and skirt outfits sound like a fashion victim crisis, but not a dress code issue. The dirty shirts and shoes are a dress code issue, and there is nothing wrong with saying so.

She might be embarassed for a bit, but it will be easy for her to remedy the situation (wear clean clothing) so it shouldn't be a huge issue.
posted by necessitas at 1:16 PM on January 17, 2007

OP: Her outfits would be fine if they fit properly. I guess I'm not putting this very well, but without pictures, it is difficult. The overwhelming impression is of sloppiness and lack of care, not of freewheeling individuality.

So are they too small, too large, too what? Maybe she has had a recent weight loss or gain and has not adjusted her self-image and clothing to her new self. Or maybe there are other personal issues reflected in the "sloppiness..."

I can't help thinking there's more to the story here than the clothes she wears. There's been a lot of speculation in this thread, but that's all it is: speculation. Is it possible to take time to get to know the new employee, befriend her, then address the issue later when you have more information?
posted by Robert Angelo at 1:18 PM on January 17, 2007

1a) Update the dress code and be very specific, it's the start of a new year, perfect time.

1b) Give everyone a $50 Target gift card

2) Get some polo shirts with your logo printed on them
posted by Mick at 1:19 PM on January 17, 2007

A personal story, don't know if it'll help or not: I had this problem once in a two-person office where I was the secretary and my boss was the--well, boss. She was pissed off because my clothes were too nice, in her estimation. She asked me to start dressing down, so that we would look different--people coming in to the office would immediately realize that she was the manager.

I told her I didn't have any casual clothes, which was true--for years, my clothing budget had had to go to work attire, and in previous jobs had always had to dress in an officey way. For her to tell me to go buy new clothes, jeans or otherwise, for a job that was barely keeping me in ramen was ridiculous. I couldn't satisfy her costuming requirements, and I quit.
posted by frosty_hut at 1:27 PM on January 17, 2007

Best answer: I framed a similar issue once as that of looking out for the professional development of my staff. Kind of like this:

So...we're all judged by our appearance, like it or not. Of course we want you to be comfortable and feel part of the group here, but your clothes come across as too casual [note: this is code for sloppy] for the position. It can be dumb/frustrating/silly, but I don't want superficial stuff to get in the way of anyone's perception of your job performance. And I don't want to embarass you, but I REALLY don't want some clod to embarass you. How can I help?
posted by desuetude at 1:43 PM on January 17, 2007 [1 favorite]

OK, mygothlaundry, upon further reflection and reading your followups, I am starting to sympathize with you more.

I'm trying to imagine what the rest of the people in your employ (a museum, I'm guessing?) dress like. Is it really that different from her? Or just less colorful? In my experience, people of any age will instinctively adapt to fit in to their environs. For instance, I detest ties, and my job does not require them, but unlike I might have done in my 20s, I will occasionally wear one anyway if I feel like it would be more appropriate to whatever is happening that day.

If this employee is really the odd-woman-out, and that doesn't naturally register on her, she just might need a little gentle unjamming. If that doesn't help, I'd vote you update the dress code, as mentioned previously, and see if she gets the hint. Then cull the herd as necessary if it still bothers you.
posted by M.C. Lo-Carb! at 1:44 PM on January 17, 2007

It seems our volunteers and board members aren't taking you seriously, and I'm having to spend time reassuring them that you're good at your job, etc. etc

Please please please please don't say anything like that!! The issue is about clothing. That makes it sound like she is incompetent at her work and on the verge of getting fired!

As many have said:

sit down with her one on one. Stress that she is doing a great job (assuming she is), then politely but firmly explain she's not complying with the dress code. It will be awkward, but that's the responsibility that comes with management- those in charge have a duty to deal with uncomfortable things directly and fairly.
posted by drjimmy11 at 1:54 PM on January 17, 2007

If you were her, what would you want your boss to do?
posted by craniac at 1:57 PM on January 17, 2007

I vote for desuetude's response. If she's great at her job, then you're doing her a favor by helping her present herself in the most positive light. "How can I help" is a much better way to approach her than "You're in vioaltion of clause C of the Offical Dress Code."
posted by junkbox at 2:02 PM on January 17, 2007

I've been in this situation as the sloppy dresser. I was dressing too casual though, not like your employee.

Let me tell you, no matter how nicely you frame it, she's going to feel a bit hurt, but she'll get over it. If you notice an improvement, compliment her on it.

So I agree with the others, firmly but kindly say that she's not reflecting the image you require, offer assistance if needed, and be sure to compliment the change. Don't overdo the compliments though, once should do it.
posted by yellowbinder at 2:14 PM on January 17, 2007

What about the old "mix two positives with one negative" type of thing. Tell her that as she's been there X weeks you'd like to have a quick review/chat about how things are going.

Dealing with customers: superb. Punctuality: excellent. Dress code: bit of a problem here...
posted by TheophileEscargot at 2:31 PM on January 17, 2007

I can't offer any advice beyond what's been stated, but if you find out money is an issue, tell us her approximate size and I'd be happy to donate some clothes. Now I'll read more upthread to see if you've already mentioned anything like that. Email is in profile.
posted by ersatzkat at 2:33 PM on January 17, 2007

This is one of these situations that is easily brought up at a regular review meeting: every X months, each employee has a meeting with a supervisor/mentor/appraisee to review any issues. A lot of workplaces shy away from this kind of thing because they think that this kind of "formality" isn't appropriate in a "my door is always open" sort of work environment. By contrast, making a small amount of time for a regular meeting of this sort can make space for precisely sort of minor issue to be brought up (whether boss to employee or employee to boss) without the oddness of having a meeting specifically about a small issue. Perhaps you need to have such a system in your workplace so that it is easy to raise this kind of issue in the future.
posted by Jabberwocky at 3:07 PM on January 17, 2007

vorfeed, it's one thing to live with a colorful employee that doesn't represent your business to your customers. I could understand your point of view if you never had face-to-face contact with customers. But in this case, it sounds extremely legitimate to request that the employee have a professional appearance during work hours.

Yes, it is. And it's also extremely legitimate for that employee to say in return, "stuff your clothing requirement, I quit". Or, more likely, quietly start looking for a new place to work. The fact that this job is a part-time position at a non-profit makes this particular outcome seem more likely to me. Personally, I don't deal face-to-face with customers often, and when I do I dress up, usually more than my co-workers do. But that's my decision, unless I was specifically told otherwise when hired, and I'm the perverse type who would absolutely quit a job over an issue like this. That's what the employee side of at-will employment is all about.

In short: I don't think there's a nice way to tell her this, because it's just not a nice thing to say to somebody. No matter what you say, she is going to grasp the idea that you think she dresses like a "sloppy, lack-of-care panhandler". You are not going to be able to avoid giving that impression, because it's exactly the impression you have of her. So tell her like a boss (lots of advice on that here), and impress away!
posted by vorfeed at 3:48 PM on January 17, 2007

>> It seems our volunteers and board members aren't taking you seriously, and I'm having to spend time reassuring them that you're good at your job, etc. etc

Please please please please don't say anything like that!! The issue is about clothing. That makes it sound like she is incompetent at her work and on the verge of getting fired!

No, that's kind of the point. The idea is mgl saying, "I interact with you all the time, and *I* know you're great. But your appearance is getting in the way of *other* people realizing how great you are, and that presents a problem for me (and you). There's an easy fix for this, which is dressing in the same way you did for the first few days of this job."

Honestly, most women pretty intuitively understand that their appearance influences how other people see them; this sort of explanation shouldn't be any big shock to her. And her appearance is causing problems among people higher up than her, which means in some sense that her job is at risk if something doesn't change. I doubt mgl wants to spend large chunks of time defending this woman to the board, and at a certain point it's going to be easier to fire her than continue to make excuses for her.
posted by occhiblu at 4:56 PM on January 17, 2007

Another vote for re-writing the dress code and breaking it down into specifics – a long list of what is unacceptable is best. The only time I ever had to discuss a dress code, I just highlighted the relevant parts of the dress code and handed it to the offender (I am not a manager, and because of stuff like this never want to be). This way I didn't have to hold a discussion which I felt was beneath our collective dignities but left out ambiguity.

I am not sure anybody really likes corporate dress codes, but its one of those (sometimes hidden) obligations we have to put up with in order to earn a living – you really shouldn’t feel bad about enforcing it. Our society talks a lot about expression, creativity, and free-thinking but very few of us are lucky enough to really get the chance to live that kind of life.
posted by Deep Dish at 4:58 PM on January 17, 2007

I think desuetude has the right idea. I get away with not exactly following the spirit of the dress code by being 1) very bloody good at my job (I hope), and 2) being very creative with everything I do. In the particular node of corporate space that I inhabit, that lets me show up wearing khakis and layered polo shirts without getting shat on. (That said, when the occasion requires it, I absolutely dress up as necessary). But not everyone can do that, and if I were in one of those positions, I would absolutely want to be addressed in precisely the mode that desuetude suggested.
posted by dirtynumbangelboy at 5:47 PM on January 17, 2007

My other half has adult ADD, I've never had a formal diagnosis but am very like him - we both fail at these sort of mostly-unspoken dress codes, in exactly the kind of ways you describe (apart from the stripes and plaid). If someone puts a gun at our heads like a job interview or some ghastly formal social occasion we can make hugely stressful efforts to smarten up. Neither of us manages these things well for any length of time.

Some people simply don't pick up these sort of social cues or find these sort of social conventions hard going. It might be worth your while trying to work out whether it's some kind of 'wiring' issue like this. If it is, then however you raise it, you won't change the person over the long run but you are likely to make them want to leave. If you are anticipating complaints, rather than actually receiving complaints, then you might want to hold off and try to work out what's behind the dress issue.
posted by Flitcraft at 6:34 PM on January 17, 2007 [1 favorite]

Consider having the chat on a Friday, thus affording her time to procure new clothing or do laundry.
posted by Kwantsar at 7:20 PM on January 17, 2007 [2 favorites]

WCityMike has it. My boss uses the strategy he suggests, "... and this is my fault, for not having explained this when we first discussed [the position]." It works like a charm. Tone of voice is sincere but non-apologetic, just matter-of-fact. You are the boss after all, and of course she wants to do her job right, so the only mistake here was that you forgot to make clear that attire was an important aspect of the position.

The "are you set up for this?" question is good, too. If she says "not really," you could offer her an advance that would be paid back from her paycheck in small increments.

Also, I don't understand these "omg, for a PART-TIME job??" comments. I've never started a part-time job without having to purchase some kind of attire. More than once in my life I have bought from Goodwill the full waitress/caterer outfit: black dress pants, black dress shoes, and a few white starched dress shirts. Yes, even when I was almost out of money and had two weeks before I'd receive a paycheck. Once I even had to order non-slip sneakers from their own catalog. Though striped socks, ill-fitting clothing, and clothing with holes do sound like "free box" finds to me. Hey, maybe you could anonymously drop off lightly-used black slacks in her size! ;-)
posted by salvia at 7:31 PM on January 17, 2007 [1 favorite]

send around a link to metafilter, drawing everyone's attention the the thread before this one. maybe she'll find this Q and figure it out herself.
just joking.

some time ago, working at a casual public-interaction job, several co-workers were judged to be projecting the wrong image b/c of their clothes. my boss instituted a very specific, but loose, dress code for all the people who faced the public. at first we all balked, but then it was okay.

we were expected to keep to a sort of style bible created by management. the overall effect was something like a starbucks or indigo bookstore dress code (they wear khaki or black pants, and a black or blue button-down shirt). it's not as lame is it sounds, and it made us all look like individual members of the same team.

we each wore different stuff that we liked and felt comfortable in- but all in the same general vein.
we were given a particular colour palette- (we had a few rich complimentary shirt colours to work with- slate, cranberry, charcoal, burnt orange, chocolate, and metafilter green, also white or black, worn with black or grey dress pants). the shirts could be button-downs, or fitted sweaters, or sleek upscale t-shirts, but nothing sexy or messy. no loud patterns, no logos, no white shoes. men could wear ties but didn't have to.

we got the style bible in an all-staff meeting, specifying stuff like how much skin could show (no belly, no shoulders), and how tight things could be (if the bra outline showed in the back it was too tight, etc).

we were also given an annual allowance of a few hundred bucks, and all purchases had to be approved before they were reimbursed. the boss pointed our noses at a few stores that had the right look that season, within our price range, but they didn't care where we shopped. getting the allowance, and a half-day of paid shopping flextime the first week, really sweetened the deal. the boss praised appropriate clothes like crazy and was gentle with her "no" judgements.

we each ended up with about five to seven tops and two or three pants, which was fine by us, and we had space at work where we could leave our "work clothes"or iron them before a shift if need be.
the whole system worked well, and i think it made our public team look like grownups.
posted by twistofrhyme at 9:10 PM on January 17, 2007 [2 favorites]

occhiblu, she's anticipated complaints, not received them:

And I am the person who will get the complaints from the elderly board of trustees members and volunteers and so on.

So, no, she doesn't get to say that she's had complaints, because she hasn't. Additionally, the only way I can imagine making this situation yet more humiliating for this woman is to bring others into it, either by addressing it as a group issue when everyone knows it's really about one person, or by saying others have spoken disapprovingly about her dress.

Just don't make this harder or more painful than it has to be. Address her one on one at a time when you are naturally alone so it feels less like she's being called on the carpet. I completely agree that desuetude's and WCityMike's approaches are best and suggest you combine them, noting that it was you are sorry you failed to mention it when she started and that you don't want her otherwise stellar performance to be judged by your error. I would further suggest that you remind her of the acceptable outfits she's worn in the past so she knows what you're looking for. You can't police good taste, so focus on the fit of her clothes and say nothing of the mismatching. Speak gently and without embarrassment. Thank her warmly for the wonderful job she's doing.

If there's even a hint of "you should know better" condescension or irritation in your attitude she will sense it, be wounded by it, and you will more than likely lose a good employee over it. Be careful.
posted by melissa may at 9:25 PM on January 17, 2007 [1 favorite]

Why don’t you take her out shopping with you, if at all that’s possible. I’m sure you’re a nice person, from the way you’ve taken care to think about this person, so I’m sure that’ll come through if you need to tell her that her attire might not be appropriate for the office sometimes. (I understand your pain—I’m not very confrontational either). But if she still doesn’t understand, then it’s not your fault.:)
posted by hadjiboy at 6:14 AM on January 18, 2007 [1 favorite]

Yes, it is. And it's also extremely legitimate for that employee to say in return, "stuff your clothing requirement, I quit". Or, more likely, quietly start looking for a new place to work.

Except in the extremely rare situation of a brand-new but expensive-to-replace employee, that outcome is not one to be avoided at all costs.

If dress code is sufficient to get someone to quit, then a million other minor issues will also be sufficient to get that person to quit. Get them to quit and get someone in there who wants the position.
posted by mendel at 9:37 AM on January 18, 2007

On further reflection, your new employee is Ugly Betty. She's "wonderful," you "love her," you just don't like the way she dresses and looks. You fear the reaction and complaints of board members and others, although it isn't clear that you've had any.

Are you sure this is really a problem?
posted by Robert Angelo at 7:39 AM on January 19, 2007 [1 favorite]

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