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What to do when your male boss tells you you dress “too well”

by C on 02/18/2010 · 170 comments

in Fashion,Wear to Work

Today’s reader question comes from a reader in a small, private firm on the East Coast…

I’ve been at my first job out of law school for 15 months. I’m 26 years old, but have a young face and often get asked if I’m an intern instead of an attorney. I am a litigator and I wear suits when I go to court, which is roughly twice a week.

Joking in the office one day, I mentioned to an Of Counsel with whom I am comfortable that I got the intern comment again. He said that, while I do have a young face, I dress “too well.” He said that I need to “be a little frumpier or dowdier.” That, while I dress well for a young, female professional, I dress TOO well for a young, female attorney. The analogy was made that I dress similarly to a middle aged male attorney who wears a blue pinstripe suit, blue shirt with the contrasting white collar and French cuff, cuff links, and a giant diamond pinky ring – just “a little too cheesy.”

Is the Of Counsel right? Do I need to wear silhouettes that are more boxy, as he also suggested? I want to be taken seriously as an attorney, but don’t see the reason to cater to ultra-conservative views on wardrobe when I would be uncomfortable in such things, as it is not my personal style.

(We’ve edited her e-mail for space; she also notes that she has a second job working at the local Express, and owns much of what is sold there; she attached the above blouse as an example.  Essential Stretch Striped Shirt, $49.50, Express.)

First: We’re not going to comment on the many, many, many things we might say about the of counsel, the propriety of his remarks, or what kind of working environment it must be.  Maybe he’s like your frumpy father or big brother and only meant to be helpful — for example, if he had stopped at the cufflinks/gold pinky ring comment we probably wouldn’t have a problem with this.  Maybe he’s a jerk, which is the vibe we’re getting from his suggestion to wear “boxy” clothes, i.e. “less sexy clothes that hide your figure.”  We don’t really know.  We might just link to this fact sheet from the government about “when to know if it’s sexual harassment,” however.  We might also suggest you contact your alumni career office to see how they recommend dealing with the situation (and perhaps if they can recommend a good recruiter).

Second:  Sigh.  The fact remains that he’s a superior to you, you still have to work with him, and worse, whatever it was that he’s projecting may be something that a lot of men (and women) around you are projecting.  So it’s time to do some soul searching — are you wearing your clothes too tight?   You may want to start buying a larger size at Express (or two) — clothes will still have a fitted, tailored look, but won’t be painted on (as they are in many of the models).  Another thing to watch out for is whether your clothes are too low-cut.  Express can be a mixed bag — there can be some great work basics in there — but there can also be some sexy going-out clothes in there.  Steer clear of the going out clothes.  You may want to peruse the website at far more conservative places like Brooks Brothers and then view your closet through those eyes — would BB sell a frumpier version of it?  With the top above (a simple fitted shirt), the answer is absolutely yes.

Finally:  We hear from a lot of women that they have issues with looking too young, and we’re going to ask our readers — how do you deal with this?  Our suggestions:  Pull yourself up tall — really work on your posture and conveying authority through your body language.  Make sure that all aspects of your outfit — your coat, your shoes, your bag — convey “grown up.”  (For example, avoid a puffy coat and a backpack.)  You may want to keep your hair pulled back in a neat (and intentional) low ponytail.

Ok, readers, we’re sure you’ll have thoughts aplenty — what are your thoughts on her e-mail? On changing her appearance for her (current) boss?  About looking too young?

(L-0)

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{ 170 comments… read them below or add one }

1 Original Poster 02/19/2010 at 2:08 pm

I am the one who originally asked this question of Corporette. Thank you so much for all of your insight, it is very helpful. I will answer some of your questions that seemed to be recurring themes:

1. Can I ask/observe co-workers: I am the only female attorney in the office, and I am the youngest of ALL employees (attorney and support staff) by 14 years. Yes, this is a problem in and of itself and the work environment is rather challenging as a result. While I would like to ask the opinion of a female co-worker, I do not have one. That is why I came to all of you!

2. Brooks Brothers/Ann Taylor/JCrew: Love those stores, but thank you to those who recognized that as a litigator, I am forced to have two jobs (and still qualify for economic hardship deferment on my loans). Not quite financially ready to shop at those places yet, but I will apply to Ann Taylor. Great idea to take out the guess work altogether. Who wants a discount?

3. Can I ask my friends: I did. I asked a point-blank, be-honest-even-if-it-kills-you question to my (male and female) friends, ages 26-38. The women shop at Banana and JCrew. My friends see how I dress and were surprised by what my Of Counsel said, which was why I came here!

4. The stereotype of Express is 100% valid, but please give me some credit. I read Corporette, after all. I know that one should not wear painted-on pants (I do buy a size up), show cleavage (buy-one-get-one camisoles!), or wear fake/chunky jewelry (see below). I got the job at this firm, so I must not have looked “too sexy” during the interview process. I never thought to take a closer look at fabric, though. I really like that idea.

5. Dark-rimmed glasses and pearls: I got this one right! I wear these every day (I’m rather blind and the pearls were from my late grandmother). I’m on the right track! I’ll keep it up.

Thanks again.

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2 Anon 02/19/2010 at 3:08 pm

Your attitude rocks. I think it is difficult to open yourself up to potential criticism and even more difficult to take said criticism (even constructive!) in stride and be positive. It is very refreshing :)

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3 LawyerMomof2 02/19/2010 at 3:51 pm

Agree w/Anon re: how gracious and responsive you were to what was sometimes harsh feedback. You sound like a lovely person to be friends with or work with!

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4 dw 02/19/2010 at 5:25 pm

I agree completely. I think the sheer volume of responses to the OP would have made many women defensive. Congrats to Original Poster for being so mature and- dare I say?- Corporettesque.

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5 Legally Brunette 02/19/2010 at 4:24 pm

OP, I loved reading your post. It sounds like you have a really good head on your shoulders and are very receptive to feedback. Reading some of these posts, I think some people were unduly harsh, but hopefully you realize that we’re all here to help each other and that the suggestions are coming from a good place. Good luck!

ps: Sign me up for the AT discount! ;)

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6 KC 02/19/2010 at 5:23 pm

Just a quick note of encouragement to OP (given after I read your post below about your weekly salary). I started out (15 years ago now) in much the same straits–working at a low paying law firm, and working at AT on the side for the discount, and worrying a lot about student loans. It will get much, much easier as you advance in your career. I’m proud of myself that I got through those first few years, eventually got a job at a larger law firm that would not have hired me straight out of school, and built a solid career. It can be very discouraging when you are starting out (especially in this economy) and wondering just why exactly you went to law school when you see friends making the same money or more with just an undergraduate degree. It can, and likely will, get much better for you. In the meantime, try to get a job at JCrew or AT on the side instead of Express–you may as well put your discount to the best possible use. Good luck!

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7 Emily 02/19/2010 at 7:43 pm

When I was first starting out in my career in the corporate arena, I was very self-conscious of looking too young, so I overcompensated by wearing suits, suits, suits. I had a part-time job at Talbots and it was by far the best decision I ever made. It was a way to get much better quality pieces then if I had worked any place else. So I support the notion of perhaps looking for a part-time position with a different retailer. Additionally, as an attorney, might you have a local bar association that offers mentoring programs or networking events? That may be a great place to find other women attorneys that could be good resources for your career as a whole, not just the fashion. I agree with other posters on fit and fabric. A button down shirt is a staple, but not if it’s too bright, too shiny, too tight, or to bizarre. I’m not saying that’s what you wear, I’m sure you don’t, but think of this as your time to “upgrade.” Buy merino instead of acetate, pants with a lining, ideas like that.
And finally, I was told I look like Rose Byrne, the actress who plays Ellen on Damages, the FX show. Her character is a young attorney. Her clothes are very flattering, but very subdued and classic.
OK, really, final point-how’s your hair, makeup and nails? Change outs for nude nails, neutral makeup and elegant hair could make all the difference:) Good Luck!!!

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8 MelD 02/19/2010 at 7:50 pm

With your budget, I’d suggest trying to go to the outlets. A lot of the clothing in BR and AT outlets really are reasonably price. In fact, this weekend the AT Outlet is having 40% off the entire store and BR outlet also has similar sales.

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9 Gail 02/19/2010 at 2:24 pm

Does anyone out there remember Congresswoman Bella Abzug? She was known for her wide brimmed hats. She explained that she started wearing hats because, as a young woman lawyer representing labor unions (as do I), she needed “presence”. 30 years ago I was young looking and short to boot (5′ 1″). ALWAYS wearing a jacket, standing up straight, and taking control was very effective and I was never mistaken for an intern or secretary. It is possible to have personal style (like hats or vintage suits) and still look professional.

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10 Delta Sierra 02/19/2010 at 3:52 pm

Bella was da bomb. I love when people develop their own trademarks, like the hats. And Madeline Albright’s message brooches. One gathers that brooches are supposed to be old-lady now, but tough, I love ‘em. I have a big collection of soft scarves, too, not getting any younger, I like a little neck coverage.

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11 R 02/19/2010 at 2:45 pm

I have lived mostly in places where the shopping was limited, Express was one of the “higher end” stores available, and I couldn’t afford to be shopping online at better stores and sending back the stuff that didn’t fit right. So everyone wore Express to work, it seemed.

I think you can pull of Express sparingly, with a lot of balance by high-end materials. I found a lined, wool work pant at Express some months ago, and bought a size bigger than I am, so it hangs straight instead of being fitted. It’s part of my regular rotation, along with an older, lined black blazer I’ll wear on more casual summer days with the sleeves cuffed. But I pair it all with cashmere sweaters, simple *real* jewelry, and neutral hair/makeup.

I work with mostly older men as well (and I also look young and have been called “girl” and “blondie” before at other jobs), and make sure I keep a no-nonsense attitude when dealing with them, saving the chatter and fun for my female colleagues. The women compliment my dressing, the men tell me I work too hard and that I’m making them look lazy, the director of our agency comes to me when he needs something done well and quickly, and I was recently introduced as one of the best employees of the entire place by one of the top men. I feel I am perceived as professional, and that’s how it should be. If I wear Express – if you wear Express – because of availability or price, no one should be able to tell but you. Pay sharp attention to fit, go for natural materials when they have them, don’t be afraid to size up for a more professional look, and make sure it’s all fully lined and fully covered.

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12 D 02/19/2010 at 3:46 pm

Sounds to me like the older counsel may be a bit clueless in terms of tact, but that he was trying his best to assist his colleague in a problem that she had presented to him. During the first year I practiced law, I too would get questions from clients to the effect of ‘just how old are you’? I switched from contacts to glasses in an effort to look more authoritative, and it seemed to work. It may be that I also also gained confidence and therefore presented myself with more authority. Another potential suggestion, call a large expensive story such as Nordstroms that has a lot of clothers for women professionals and make an appointment with a personal buyer – and tell the buyer what your issue is, and that you are looking for one or two pieces that will help address it and more going forward as your salary increases, loan amounts decrease etc.. Go in to the store in one of your going-to-court outfits, and ask the buyer for an honest critique as a starting point. None of us on the board can see you, and therefore our advice may be falling short of answering your issue. Failing that , time should take care of it – I am happily back n my contacts.

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13 Chicago K 02/19/2010 at 4:09 pm

Second that your attitude rocks – I am not entirely sure I would be able to get through all those comments if I were the original poster!

Let me take a different spin, knowing that you work with all men. I work in banking, in an all male department. And I have heard comments from them saying, “You dress too nice, you put the rest of us to shame!” I buy everything from the suggested places of Ann Taylor, Banana and J. Crew. In fact, almost exclusively so. I wear pearls because I love them, not just because they are in this season. Given my experience with my male coworkers, It could just be that 1) They have little idea what professional looks like if not frumpy 2) They don’t dress as nice as you and they don’t know how to without it feeling “over the top.”

Do the men in the office have any style? In my office, they certainly don’t and I do stick out a bit being female, young, and dressing well. I would never in a million years take fashion advice from them…and while I don’t want to make myself feel “better than them” or some much, I attend to keep dressing the way I like too. Which is professional, classic and classy.

It seems you dress that way too…and it may be entirely correct that this guy might just not know what he’s talking about!

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14 Karen 02/19/2010 at 5:22 pm

Agree with the comment about women from the marketing dept – it may be that even though you are not wearing any single clearly inappropriate item, the overall look is just a little more form-fitting and a little more dressy than is typical for female attorneys. The stylish women lawyers I know seem to incorporate one stylish item in anotherwise business-like outfit, while the marketing personnel have several “look at me” items on. One colorful blazer, shiny shirt or dangly set of earrings = fun, all three may come across as trying too hard / caring about form and not substance.

I also looked much younger than my age when I started. In addition to the great advice already posted, I recommend not smiling too often or too quickly. It makes you appear eager to please and therefore young.

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15 L 02/19/2010 at 5:42 pm

Is it not possible that this guy is just not a very good dresser himself/doesn’t want to have to dress too formally, and here is this young whippersnapper in suits and dressy clothing making him look bad??

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16 HK 02/19/2010 at 9:48 pm

I work in a large law firm known for being a little quirky. Style is fine, but it only works if executed with modesty. Some simple rules for looking conservative without being plain:

*If you can see the bottom curve of your bum, the pants are too tight.

*The shortest skirts should be just at the knee. A pleat is ok, a slit is not. If you insist on a slit, it must be an overlap slit, not a V.

*More shoe than foot.

*One unusual item (fancy bracelet, brightly colored shoes, funky belt, fun nail polish) per outfit. Only one.

*Nothing that looks like underwear: no lacy camis, no spaghetti straps.

*Top button can always be open. The second button can sometimes be open. The third button is only open for playing sexy secretary.

*No armpits. No toes (unless you’re really sure that a peep-toe is ok).

*Nude bras. White undershirts. I shouldn’t see evidence of your bra but I should know that it’s not your skin under that shirt.

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17 M 02/20/2010 at 3:40 pm

If anything, the outline of an undershirt sounds more revealing than someone’s attempt to imagine that there is skin under your shirt. :)

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18 HK 02/20/2010 at 6:15 pm

I guess for me this comes into play when I’m wearing a see through shirt over dark pants and the waistband of the pants is slightly visible through the shirt or when the pocket or placket of a white shirt makes it obvious that the fabric is a little transparent. I want someone to know that they’re not, in fact, seeing through my shirt.

I absolutely agree with you though where the situation is one in which I’d essentially be advertising my undergarments.

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19 BethInNY 02/19/2010 at 11:24 pm

Re: OP’s #2 above — you could try AT Loft, esp their sale sections — just need to be careful not to get anything too casual (and unfortunately, with spring/summer approaching, it may quickly get too casual).. But I’ve found some good, appropriate pieces there, at much lower price points than AT, B Bros, etc. Also, I don’t find BR too expensive when you shop their sales — give it a shot and see if you can find something!

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20 MelD 02/20/2010 at 9:01 am

Unfortunately ATL has gone ultra casual this season. I can’t remember seeing anything in there that would be remotely appropriate at work. It’s all cargo pants/distressed jeans, glittery t-shirts, and short skirts. Hopefully it will improve because I’ve found lots of work-appropriate clothes there for <$20 on the sale racks in the past.

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21 BethInNY 02/20/2010 at 1:29 pm

Yeah, agree. It’s unfortunate the direction they’re going in, but sometimes they have more stuff online that looks a bit better.

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22 BethInNY 02/19/2010 at 11:24 pm

*BR = Banana Republic

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23 Maren 02/20/2010 at 5:09 am

Depending on Of Counsel’s age and your practice/geographic areas, when he says “frumpy” he may have the image of a much older female attorney in mind. When I used to work in family law in a semi-rural suburb, all the female attorneys were older and wore suits with boxy silhouettes, definitely tending towards the frumpy. If you’re the only female attorney in your office, he may simply not be used to working with someone younger and more fashion-forward. Just an optimistic thought!

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24 Pinkrobot 02/20/2010 at 5:25 am

Amy–
Anon #152++
OP++
Education is an investment in yourself, generally a very safe and sound one. but like all investments, it carries risk.

there is no such thing as a ‘sure’ job post school now, except maybe the military.

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25 Corinne 02/20/2010 at 8:45 am

Dear Original Poster & Friends,

Some insight: so that you can see I can relate to your message.

I am 32 and constantly am mistaken for being in my early 20′s. While my female friends remind me to be grateful, my appearance makes it is a constant challenge to earn respect and the assigned wisdom/knowledge/experience that comes with age. To boot, I’m large-chested. I look far from the business “type.” I can see that it would be hard to take someone who looks like me seriously.

Now, for the advice:
Your message reads that you’re doing everything right from a fashion perspective. Kudos!

My advice to earn the respect and overcome the “young” stereotype: Fight for opportunities and seek out opportunities to prove your worth as a viable resource. I’ve done this and continue to experience positive results. I’ve gained exposure with work colleagues, during which I’ve communicated my age and prior work experience. They have come to rely on me and trust my knowledge, and (in most cases) the stereotype has been put to rest. As a result, I’ve built a reputation that supersedes my appearance.

Best wishes for continued success!

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26 BethInNY 02/20/2010 at 1:26 pm

Based on the Of Counsel’s actual comments and the OP’s additional post above, I have a differnt interpretation of his comments. It sounds like, by telling her she dresses like the guy w/ the pinky ring or whatever (i.e., too cheesy), and given that OP says she does wear pearls, and suits several times a week, I think he was trying to tell her NOT that she was dressing too “sexy” but that maybe she is trying too hard / looks a bit like she’s wearing her mother’s clothes.

Just an additional perspective, this could be off too, but I don’t get any of the “too-sexy” vibe from his comments, and it seems like the other posters are only picking that up because of the side job at Express. So – OP – maybe dressing more grownup is not the answer, the answer is instead finding some way to dress your age and not look like you’re trying too hard to dress in a way that’s not ‘you’.

Hope this helps..

And btw — meant to post this earlier — seriously, C, linking to a page on sexual harassment? Really? His comments didn’t even come close to that, IMO, and it’s unfortunate that men have to tread sooooo gently just to provide friendly advice to an employee, when they came to him in the first instance for the advice! No wonder men are (sometimes) scared to say anything to a younger female employee, for fear of anything out of their mouths being labeled harassment!

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27 L 02/20/2010 at 3:51 pm

Agreed. I didn’t at all pick up a sexual harassment vibe from the description of the conversation. It sounded more as though he was trying awkwardly to be helpful, while trying to be really careful to avoid saying anything that could be construed as offensive. Since there’s no other older women in the office to give her this type of feedback, he couldn’t ask someone else to give her feedback, which is what I usually see happen when there’s an issue with someone’s clothing.

More importantly, I think the attitude of always looking for potential sexual harassment in interactions that are awkward for other reasons can really put a damper on the ability of an older man to give well-meant constructive feedback to a younger woman.

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28 Cindy 02/21/2010 at 6:50 pm

My thoughts exactly. The comments did not seem directed at “too sexy” as much as “too much.” Relax, dress your style–in an appropriate business fashion of course, and try NOT to look like you are trying too hard.

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29 Texas Law Chick 02/22/2010 at 1:11 pm

I also look very young for my age and have a very young sounding voice. I was once told by a more senior woman partner (not in my section) who was frumpy, that I needed to downplay my looks so that people would take me more seriously. Someone later asked why I was so serious all the time at work when they ran into me in a social setting. You can’t win trying to please everyone. Since then, I have learned to embrace my looks and my personal style. I found that when I was comfortable with what I was wearing and with my demeanor, clients were too. Being the only woman in my section paid off as clients wanted to work with me instead of with the frumpy boys. The biggest piece of advice I have for you is keep your current style but absolutely make sure that you are the best and brightest. Your appearance (whether you get noticed for your age or your style) will bring clients to you, but they will stay with you if you back it up with sharp legal skills and strong work ethic. Once they like working with you, they won’t notice your age or your clothes.

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30 Chicago K 02/22/2010 at 2:49 pm

Great advice!

I get a lot of conflicting responses from people at work too…”Gee, you are so quiet” “My goodness, you are too social!” “Too serious” is another one I get. You can’t always win, but confidence trumps all of them, IMO.

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31 Tsippi 02/23/2010 at 6:21 pm

Two things I wish I had learned 20 years ago:

1. When you ask a man for advice, or tell him you have a problem, he often feels obligated to provide advice or a way to fix the problem, whether or not he actually is secure in what he is saying. It is part of the charm of the men in our lives. The trick is to consider the advice on its merits. Maybe it is valuable; maybe he just couldn’t bring himself to say “I honestly don’t know.” That is not a criticism of men. It is part of their charm — and part of the reason I take my problems to them. At least I know I may actually get a solution set.

2. The hardest situation professionally is to be the only woman in an office, or the only young woman in an office. I have been in one or the other category for 25 years. Comments, jokes, and sarcastic put downs about you being yourself will make you think you need to act like a man. In your attempt not to smile so much, to be less cheerful, and not to say nice things about people — not to mention never to wear anything colorful or fashionable — you will slowly drive yourself mad. You will be miserable. And you will be sabotaging your career. The high quality men in your office appreciate women being women. I am finally at the top of my profession. I am still the only woman at staff meetings, but the men who used to make sarcastic comments about my “lack of gravitas” are now junior to me. My boss — an immensely powerful person — sent me a note at Christmas: “Thank you for brightening up the office and taking care of people around you.” Twenty years ago, I would have been offended. Now I know he appreciates me being me. Find a way to be your essential self.

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32 AAS 02/25/2010 at 11:57 am

This might sound weird, but as another young woman (we’re the same age), what I have recently tried and found has made me look older is dying my hair. I have never dyed my hair (except for hot pink streaks in college) because I was always happy with my natural color. Recently on a whim I dyed my hair more natural colors, although you can tell that it’s not my natural hair. For some reason, I have had several people tell me that I look older this way.

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33 gina 02/25/2010 at 12:38 pm

Maybe lay off the suits except when going to court and start wearing clothes slightly closer to business casual. Maybe something young yet professional like many of the cardigan-blouse-skirt-or-trouser styles in the recent J. Crew catalogs. Professional, modest, work appropriate, uses the wardrobe you already have, but mixes it up in a slightly younger, less formal trying-too-hard kind of way.

Also, someone who says that in order to appear more professional I need to dress “frumpier” is not someone I’d be too quick to take specific fashion advice from.

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34 don't hate, it's true 03/10/2010 at 4:04 pm

She looks like she’s an intern because Express makes cheap, shitty internwear. I would probably mistake her for an intern or (if she looked older) a secretary, too.

She doesn’t need clothes that are boxier — she needs something more sophisticated. She should look for items with rich, subtle textures, and should try some more mature jewelry (the requisite pearl of faux pearl studs would be fine).

Brooks Brothers is a good recommendation, but their clothes *are* boxy. She could also do okay at Theory. Their silouettes are less dowdy but the fabrics and details impart some complexity that shitty shit clothes lack. For a splurge I would also try Ports.

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