A recent SNL episode featured a fictional campaign advertisement for a mayoral candidate.  The character, Glenda Okones (played by Kristen Wiig),  listed her flaws, including her reputation for being harsh and cold.  “Here’s why,” she said:  “I just have a naturally frowny face. Not ugly, but certainly severe looking.”

Ah, perfect, I thought: an opportunity to talk about bitchface.

I’ll admit: the main reason we haven’t talked about it before is because I didn’t want to use bad words in the headline of the post!  But I think this is something that can affect a professional woman’s career, and something we should talk about.

Now I admit, wholeheartedly, that I have a naturally frowny face.  A reader once remarked that in my videos I’m always super smiley — it’s primarily because I end up looking super annoyed if I’m not.  (If I have time I’ll have to dig out some scrapped footage from the Lancome sponsored post — I couldn’t believe the video editors got so much usable footage of me looking serious because when I sent it in I worried I just looked bitchy.  Here:  me, serene but not smiling , versus me, actually pissed off.) I think most times it doesn’t matter.  After all, if I’m talking with people they can usually tell that I’m not super annoyed, and if I’m not talking to people (such as if I’m just walking down the street), I don’t really care what you think of me.

That said, I can think of at least one time this trait affected me professionally.  A few years ago I was part of a very small trial team in federal court in Philadelphia.  After a few days of trial, I grew weary of the high calorie, rushed lunches my colleagues ate, and so I excused myself and ducked out to the Subway across the street… and promptly found myself in line, in a very small shop, with all of the female members of the jury.  The first thought that went through my mind was panic — should I turn and walk out?  (I stayed. Which, looking back, was probably the wrong decision.)  Would they recognize me?  (Of course they would — it was an empty courtroom every day except for the lawyers, jury, judge, and occasional witness.)  Should I try to make conversation?  Compliment someone’s bag?  Talk about the sandwich I was looking forward to?  (I decided not to speak unless spoken to.)

Having made all these difficult decisions in the space of about two seconds, I was left standing there wondering what to do.  I didn’t want to fiddle with my phone or Blackberry — they might see some private conversation or think I was self-absorbed.  I realized that, no matter what they thought of my case, my fellow attorneys, or my behavior during the trial, I wanted them, above all else, to not think I was a total bitch.  I didn’t want it to come up in the jury deliberation room — “oh, the side with those stuck-up New York lawyers?” — and I didn’t want it to come up in the back of their minds.  In fact, never in my life had I wanted to look so approachable, so reasonable, so likeable, as I did in those few minutes… and that includes the first time I met my future in-laws.

What I wound up doing was studying the menu — like I had never been to a Subway before in my life! — and doing my very, very best to think happy, contented thoughts.  I thought of my then-boyfriend (now husband), and our upcoming trip to Paris.  I thought of a great sale that I’d been to a week or so before.  I thought of a funny inside joke my brother and I have shared for the past 25 years or so.  And then I ordered my sandwich (being extra careful to say please and thank you), and got the heck out of that Subway shop.

Ever since that Subway experience, I’ve wondered about bitchface.  Can it really affect you professionally?  I can imagine that I probably looked like a bitch when I was taking notes in all of my classes, particularly the classes where I wasn’t engaged — did teachers think less of me because of my naturally frowny face?  In interviews, many people say the first impression, such as seeing someone in a waiting room, is what matters — should I always attempt to “think happy thoughts” during those time periods?  Does it matter that this is one of those peculiar female problems — for example, how many male politicians and trial lawyers tell themselves to think happy thoughts during their moments in repose?

Readers, what do you think?  Do you think you have a naturally frowny face — and how has it affected your professional life? 

Have you ever been denied a promotion because you were too good at your current job?  Reader N suspects this may be what’s at play at her workplace, and wonders what she can do about it.

I just read your article “Getting the Work You Want” and I wanted to ask a follow up question. I’ve found myself in a position of getting passed over for moving into a complex litigation team, despite having openly expressed my interest, and my superior agreeing that I would be better used in that area. (I’ve had this reinforced by rave reviews for my senior attorneys and from fellow co-workers who I’ve helped out.)

From what I can tell, it seems that my superiors (and theirs) place more value in the fact that I can manage my workload and simultaneously back up three to four people at a time. I’ve backed up coworkers in the complex team, too, but as for moving up with them permanently… nothing.

So what’s a girl to do when I have spoken up and asked… and nothing happens? Have I shot myself in the foot by having quality and quantity? Should I just take the rave reviews and recommendations and look for work elsewhere?

Fabulous question. There are a million reasons why people don’t get jobs and promotions — including not being right for them.  That said, something I’ve seen happen is when a boss keeps a “good worker” in the trenches because his or her own life is made so much easier by the worker.  The boss knows the job will get done, and done well. He or she doesn’t have to hire or train anyone new.  It’s great!  For the boss, that is.  For the worker (which may be Reader N, here) you don’t grow at all.  For a particularly selfish boss, he or she may also try to restrain you from working with other people, give you lackluster reviews or recommendations to keep you with them, and maybe even talk down to you to make you question whether or not you “deserve” better than your current job.  (Pictured: Held back, originaly uploaded to Flickr by Matthew Wilkinson.)

This is one of the reasons why it’s so important to be the master of your own career.  You need to be the one constantly assessing where you are — and speaking up until you get to where you should be, even if that makes you feel pushy.  If you do find yourself in a situation where a boss is holding you back, in my opinion, there isn’t much you can do about it beyond getting away from the the toxic personality. And if that means taking a new job, so be it.

However, I would give every boss the benefit of the doubt — once.  For example, here, Reader N says “from what I can tell” — N, have you spoken to your superiors about why you didn’t get moved to the area you wanted?  This is a 100% valid question. Approach it with a learning mindset — be as far from “entitled” as you can be. Frustrated is fine — exacerbated even — but be careful about crossing into “angry and emotional.” Sit down with your superiors, show the different ways that you made your preference known, the positive feedback you got, and then express your confusion over the lack of movement that followed. I’d also ask when you can next expect to be moved to your preferred area.

Once you have their official answer, look at it objectively.  Maybe you were lacking a certain skill.  Maybe Person X had more of the skills needed.  Maybe they wanted to keep you in your current department until a particular big project finished.  Maybe a more formal process is required for a move like the one you want.  Whatever they say, try to make sense of it.  It’s still fair for you to get angry, and it’s still fair for you to look for a new job — but it’s also fair to say “Oh, that’s what happened,” and then sit tight until the next window of opportunity arrives.

Readers, have you ever been held back because you were doing too good of a job?  What did you do about it?  What is your general approach if you don’t get a promotion you’ve lobbied for?

There was an interesting article in Forbes the other week about how power women wake up early, and commenters seemed interested in talking about it more, so I thought we should explore in an open thread. How early do you get up? What do you do with the time? Any tips that make it easier to get up then? For those of you who don’t rise that early, do you have another special time of the day? (Sunrise, originally uploaded to Flickr by killthebird.)

For my $.02: I was always a night owl when I was younger. Term papers and graduation speeches alike got written in the hours between 12 and 3. I realized this was a problem sometime around high school when, reading a college admissions essay I had thought brilliant the night before, I realized a good two sentences were devoted to “finding a piece of licorice on the floor.” And not even in a metaphor way, just a “Kat had a dream while typing” way. Still, the habit perpetuated until after law school, I think. By then — working crazy long hours — I realized that my best time truly was first thing upon waking. So I started getting up earlier.

I also realized a funny thing: that the time was truly mine when I got up earlier. I wasn’t rushing out the door to get to work. I had time (and energy) for a workout. Then I truly got greedy and realized I could get the ME stuff done then — the stuff I’d always wanted to do but never had the chance to. I attempted to finish NaNoWriMo in the hours between 4:30-6:30 one November. I read books I had meant to read in college but never gotten around to — thinky books that won National Book Awards, and not just the latest brain candy. I started this blog. (In fact, most of the longer posts for the first six months of this blog were written primarily in those morning hours.) Occasionally, I would even use this “super Kat” time for good and do work work (usually when I was up against a deadline and needed super focus to get it done.) I love these hours — time to myself, and time to be proactive rather than react to the day.

All that said — I’ll admit it’s really hard to get up, especially when it’s dark outside. I’ve found that it’s helpful to set the coffee the night before, and also to put my workout clothes in the bathroom so it doesn’t take too much effort to change into them.  I also tell myself, “If something is important to you there will be time in your schedule for it somewhere, and now is that time.”

Readers, how about you? Do you rise and shine early — and do you use it for “me” time or productive work time?

Reader C wonders who the happy lawyers are… but I think this leads us to a bigger question that will hopefully make for an interesting discussion: how do you view your career in your general quest for happiness?

Hi Kat, I have a question for you and your incredible readers. I am an undergrad applying to law schools now for next fall and I do recognize the oft-quoted “realities” (from friends of family, professors, etc) of being a lawyer- mountains of dense reading, long (sometimes extremely so) hours, getting stuck in a job you hate just to pay of the $200k of student loans your education cost you. I sort of stumbled onto the idea of law, I wasn’t one of those who dreamed my whole life of putting away the bad guys or anything; I randomly found it through a class but I have never been more in love with a subject. I am an avid Corporette reader, but the things I read in the comments section of many posts terrify me and leave me to ask, rather desperately: Is anyone happy being a lawyer? I know everyone is different, had a different idea of “the dream lawyering job,” reacts differently to stress, etc. but if there is anyone out there who loves being a lawyer, it would be a huge comfort to hear about it!

First off: apologies to the non-lawyer/JD students among Corporette readers; hopefully our discussion will take us to greater truths about happiness and your career.  That said… reader C’s question is a great, great question, and I think the readers will give far better answers than I will considering that I never really found my happy sweet spot in the law, personally. Something I’ve heard often, and agree with wholeheartedly, is that there are two kinds of people: those who enjoy law school, and those who enjoy the practice of law. I am totally in the first camp of people — I loved law school, which I found to be filled with ethereal questions that you can ponder at your leisure and come to your own conclusion. There are clear paths to “success,” and good work is tangibly rewarded with grades and other honors. (Pictured: Rainbow Valley, originally uploaded to Flickr by rwangsa.)

On the other hand, I found the practice of law (and to be clear, my experience is mostly limited to BigLaw litigation) to be better suited for people who loved debate — you’re not picking the “right” answer for yourself, but arguing whatever’s best for your client. The practice of law involves both customer service (and in BigLaw they expect you to be always responsive) and, the higher you climb up the ladder, sales — in that you’re expected to wine and dine new clients to bring to the firm. There are not many tangible rewards for good work, at least in Big Law — everyone is paid the same, and whether you win or lose a case often has very little to do with the level of effort on your part. The drudgery quotient is also high, at least at the beginning — lots of doc review and case-hunting (where partner says, “I need a case that says the sky is blue — go find it.”).  There’s also often an element of “you must learn your client’s industry and business inside out so you can understand the documents you’re preparing or the arguments you’re making.”  All of this isn’t a bad thing, per se, but when you hear about the high number of unhappy lawyers I think it’s often because people went into it thinking they “like to write” or “loved thinking about legal questions” and find themselves in a customer service and sales position.

That said — there are LOTS of happy lawyers, and many of them read this blog. In reader surveys, people consistently say that they’re happy with their work on an intellectual, monetary, and lifestyle basis. I’ve noticed more than a few comment threads where people talk about their love for their job, and some of the older readers even noted that they had to switch jobs numerous times or that they had to work for 15 years before they found their happy place.  (Way to be persistent, ladies!)

The other thing to mention (especially to a college student) is that I’m not sure I put stock in the idea that your job is going to be your ultimate source of happiness and fulfillment — after all, they do pay you do to it.  I think it’s better viewed as primarily a source of income (and possibly accolades) and certain types of happiness, such as the society you keep at work as well as the intellectual stimulation the work provides to you, weighed against the stress inherent with the job and the time your job takes you away from other things.

So let’s talk about this.  Readers: If you’re in law, are you happy?  For those readers who’ve been lawyers for more than 5 years — what facets of the job do you enjoy the most?  In general, ladies, how do you balance the “work” nature of work with this broader idea that we want to be happy and fulfilled most of our waking hours?

So a few weeks ago there was this survey: more makeup makes you look more competent. Or so they say. This seems like exactly the kind of thing we should explore here… hence today’s open thread.

So here are some of the pictures they showed to test subjects. And I thought I’d share my thoughts (I typed these specifically for the first row, but really they sort of apply across the board).
- Picture 1: Aww, is she a college student on summer break? (Which is really interesting, because while we’ve talked about young women feeling unprofessional if they’re not wearing makeup, it isn’t a bias I generally think I have.)
- Picture 2: Meh. No opinion. She doesn’t look very friendly.
- Picture 3: Ok, if I were this chick, this is probably the amount of makeup that I’d be comfortable wearing on a daily basis, at least at the beginning of the day. That said, does it affect how I feel to look at her as a potential colleague? I suppose it does, but it comes back to me — she and I both feel comfortable putting the same amount of work into our makeup and outfits, so we must have similar/same outlooks on life. Great!
- Picture 4: This is the “glamorous” look. Maybe I’ve been hanging out with fashion bloggers too long, but she doesn’t look particularly glamorous to me. She looks kind of like the villainous boss in a movie. Is it because of the makeup? Because of the darker brows and lighter hair? The expression? This is also interesting, because according to the study, “women in glamorous makeup were found to be less trustworthy.”

The thing that I kept thinking while looking at the pictures, though is this:  expressions are huge.  I’ve worked with a lot of young newbies starting their first job, and thinking back to that first meeting, whatever impression I had of them was formed not through abstract things (like their makeup, or even their clothes) but rather their expressions.  If someone comes into your office, plops down and gives you the dead stare seen in each of the 12 pictures:  you curse the hiring department.  Whereas, if she’s eagerly listening to what you’re assigning, and maybe even suggesting other avenues for research or development — it doesn’t matter if she’s wearing buckets of makeup or not, you think, WOW, it’s gonna be great to work with her.

So let’s take it back to the realm of photographs.  Would you want to work with her based ONLY on her picture?  Honestly, I wouldn’t want to work with any of the women in this photo — they all look humorless, tired, and a bit wary.  I’ve advised this for corporate photos, and I’ll advise it again here:  your resume and your achievements are usually posted alongside your photo, so the main thing your photo needs to convey is friendliness.  Forget “smize-ing” (as Tyra would say) or trying to give some smoldering look of sheer intelligence… just look like someone trustworthy, responsive, and friendly — the kind of person you’d want at the other end of a phone line if you’ve got a problem.

I’m not saying that makeup doesn’t matter — but I think it speaks to judgment calls you make.  The woman in the third row — her first picture makes her look tired, weary, as if she is so overworked and overstressed that it is all she can do to get a shower in and show up at the office on time.  Her fourth picture (with the heavy lipstick) makes her look high maintenance, even vain, to me, because I know how much work maintaining that dark perfect lip must take. Women wearing the completely wrong color of lipstick similarly get dinged — they look like they haven’t done a self-assessment in a while.

I don’t know (um, obviously): readers, what do you think?  What do you think about the women in the photographs? And do you think those thoughts translate to makeup… or that the bigger thing you’re evaluating in the photos is the expression?  Do you take anything away from the study re: how much makeup to wear for the office?

Reader S has a question about how to ask for the work she wants…

I am a second year associate at a big New York firm. I am in the corporate team and we rotate through two specialty groups within corporate before choosing a specialty. For my first rotation I was assigned to something that I was not at all interested in. I have been able to get a lot of good experience in this group, but it is important that I am placed in a group I am interested in for my next rotation. Can you give me some advice about networking with the partners on this team and letting them know I am interested in working in their group? I thought about asking them to meet to discuss the type of work their group does but the thing is I know what type of work they do, I have spoken to all the juniors in the group so I am familiar with the type of work that I would be doing…I am not sure what I could ask them that would not seem ingenuine. What do you think?

I think this is a really important question — often you need to be vocal in order to get the work you want. (Pictured: Any Given Saturday, originally uploaded to Flickr from She Who Shall Not Be Named.) Here is what has worked for me:

1. Ask outright. Look at this as a mini job interview and remember, as with every job you want, that this is really about what skills you bring to the table to help the partners, and not about what you would get out of the work. For example, “I’m fascinated by [your area of expertise] and would love to help you on your next case.” is OK, but if you can, go even further in pitching yourself — “I was always top of my class in [X], and I’ve heard that translates really well to work in [Y] — please let me know when I can be of help.”

2. Read. Sign up for every newsletter and news alert you can on the subject matter that interests you, and study that reading material. This is all the better if your company circulates hard copies of publications because the partner “experts” will see your name on the list of people getting the publication. For example, in my law firm days, when I wanted to work on media-related legal matters, I signed up for all sorts of things, from the Columbia Journalism Review to The Index on Censorship. There were 200+ lawyers at the firm, but the circulation lists were very short (and they were printed on a sheet of paper affixed to the magazine, so you could see everyone getting the publication). It was often just me, 3 or 4 other lawyers, and then the VIP partners. Guess who they frequently called when they needed a new junior associate on matters?

3. Inform. If, in your reading, you come across something that you think the partners would want to know about (but may not have seen otherwise), pass it along to the partner with a friendly note: “I thought you might like to see this.” If there are mingling opportunities with the partners you want to work with, this is the perfect way to let them know that not only are you interested but that you are up to date on your readings. Discuss the latest case that was handed down, or a major move made by one of your client’s main competitors. The partner may or may not want to talk about it, but he or she may want to continue talking to you. When I was in law school, I knew a very young professor who attributed all of his success to something like this — he was on a circulation list for a rarely-read publication and saw an article of interest. He passed it on to the Powers That Were at his firm, and they kept coming back to him and promoting him.

4. Ask again (and perhaps ask some of the people senior to you HOW to ask). For example, shooting an email to a partner is the most non-confrontational way to ask for work — but an email can easily get buried. Another story from my past: A number of people (older associates, former associates, even partners) had told me that the way to get work in the area I wanted was to “just knock on the door and ask!”  This seemed wildly pushy to me — interrupting a partner?  To ask for work?  By dropping by his or her office?  But I swallowed my fears and I did it — I’d just “happen” to be passing by the partner’s office, and if the door was open and he or she didn’t look too busy I’d poke my head in and ask, “Need any help with anything right now? I’m looking for work in __.”  And it worked!  (Similarly, it may help to know the process — understand how work is assigned in your company or firm; this will help you figure out who and how to ask for work.)

Readers, what are your tips for getting the kind of work you want? Any glory stories to share?

I thought it might be interesting to have an open thread about some of the most stylish professional women we know personally. I would suggest we avoid names and, instead, focus on painting a picture of the women who inspire us. I also suggest that we limit this to women we know personally, not famous people — unless you see the person every day it doesn’t count.

Personally, I’m lucky to have almost too many women to inspire me! It’s funny to me that some of the most stylish professional women I know are also some of the most senior and successful women I know. Some of the stylish women I remember the most…

• When I was an assistant editor at Family Circle magazine in my early 20s, the editor in chief of the magazine was stunningly put together every day. Beautiful suits that never looked wrinkled… shoulder-length blonde hair that was somehow perfectly coiffed — it had volume and bounce and curl. She had 2 or 3 children under the age of 15, also, if memory serves — no idea how she did it.  She was an extremely intelligent woman who had interviewed for an assistant editor’s position and, when asked what her ideal job was, had said “editor in chief of this magazine” during the interview — and 15 years later, there she was.
• A female partner I used to work with also stands out in my mind. She had silver hair, just below her chin, and had a collection of eyeglasses that all had a bit of spunk to them. I remember admiring her Chanel bags and her Valentino suits — and her extremely, extremely successful career in a niche practice area. She had a very low voice, and a dry sense of humor.
• The third I’ll mention is another female partner I used to work with.  She was the first woman to make partner at the firm, and I marveled at her ability to write the most ladylike “f__ you” letters to our opponents. I remember her very simple pieces of clothing (mostly black or gray trousers, black or cream jackets, a few solid colored silk tees) and her beautiful, colorful collection of Hermes scarves. She told me once she wore the scarves because she found tags at the back of her neck to be itchy.

Looking back, I think it’s interesting that all three had some of the same things in common. For example:

• They nailed the hair. Each of these women had figured out a hairstyle that worked for her (flattering and, I’d imagine, easy to do) and she wore it that way, every day — there was no frizz, there was no sloppy ponytail or bun, and there were no “wow she’s really past her appointment to get her roots done.” Perhaps it’s a reflection of my own taste that each woman wore her hair loose, and not done up in a French twist or whatnot.
• They went for quality over quantity. I wouldn’t say that any of their wardrobes were extensive — instead, I probably saw the same pieces repeat once every two weeks or so — but they all wore quality items of clothing that fit them like a glove (nothing too tight or too loose) and were well-taken care of.
• I primarily remember the woman — not the style. Nothing was overly trendy or of-the-moment (and nothing ever seemed dated) — and her style didn’t speak louder than her words. That said, each woman took her own risks — the funky glasses, the colorful scarves — and had, I imagine, fun shopping and putting together her working wardrobe.

All right, readers, who are your real-life style inspirations? What lessons have you learned from them (tips and tricks you’ve picked up and implemented), what lessons CAN you learn from them as you think about them today?

I was reading an article recently and came across this quote:

“Someone told me not long after I moved to New York that in order to succeed, you have to understand which rules you’re supposed to break. If you break the wrong rules, you’re finished. And so the easiest thing to do is follow all the rules. But then you consign yourself to a lower status. The real trick is understanding what rules are not meant for you.”

This really resonated with me — they often say that girls follow too many rules and I know that’s been true with me. Penelope Trunk’s post (which is an entire other ball of wax) indirectly referenced this also — that girls should do less homework, apply to business school before the conventional “time” to apply, and focus on finding a husband instead of her career in her late 20s.  (Pictured: Police Officer Breaking the Law, originally uploaded to Flickr by Call to Adventure)

So I thought an interesting question for the readers would be: what rules should you break?

Personally, one of the rules I realized I needed to break was a silly one: that one shouldn’t swear around one’s superiors.  I’m not saying I was dropping the F-bomb around the VIP partner I worked with, but frequently when I was working with men about 5-10 years older than me (and especially where I was the only chick on the team) I would realize, at some point, that they were holding their tongue around me.  And I had to be the one to break the civility barrier, and then it was all cool.

Similarly, someone told me that when you’re working with a persnickety boss you should forget whatever you think are the priorities for the job, and focus on what the boss’s priorities are — that your success or failure in those areas will determine whether the boss sees you as a success.

Readers, what rules have you learned to break?

Reader S has a great question about how to grow her leadership skills as a young female executive…

I’m not sure if this has been discussed before, but I’m looking for recommendations–either from you or your readers–on some good leadership skills workshops/trainings/webinars. I’ve recently been promoted to the executive team at my company. While my initial reaction was excitement, I’m now starting to feel a bit out of place at times. The promotion was given to me as a “stretch” role, which the CEO defined as a bit of a leap of faith. He’s confident that I’ll be comfortable in the role and gain the skills necessary in short time, but ever the over-achiever, I want to quell my discomfort ASAP!

I’m finding myself acting a bit more assertive and, well, tough in the negative as opposed to assertive and confident. It’s a natural “defend my right to the role” mentality whenever I’m questioned on anything. But, I know signs of a true leader are to emit the entitlement to the role through leadership and confidence.

On top of all this, I’m somewhat young (35–the youngest member of the exec team) and am a mom to 2 children (4yo and 18mo). I’m wondering if there are any good leads or advice from working women in similar situations?

Huge congrats — this sounds like a great accomplishment, and I applaud you for trying to stretch yourself to get to the next level.  I think this is a great question, because it can be difficult to grow your leadership skills. Ultimately, I think Reader S needs to focus on a) what you think you’re doing well (so you can play to your strengths), b) what you think you need to work on (so you know where to focus your reading) and c) who to ask for feedback (and when) so that you have someone else giving you some feedback also. (Pictured: Follow the leader, originally uploaded to Flickr by jtu.)

Re: outside publications, there are a number of publications you can sign up for.  Some of my favorites:

Inc.magazine (probably about 1/3 of their content talks about leadership — see also Fast Company) — some content available on the web but may be easiest to sign up for a subscription

If you have a close mentor who’s above you, maybe ask them to sit in on a meeting you’re leading so you can get their feedback on how it’s going.  If you’re particularly close with a subordinate (even your assistant), have him or her sit in on a meeting so that you can get his or her feedback also.  Remember that about half of being a leader is in how you act — if you act competent and sure of yourself, people will respond to you in that way.

Finally, figure out if your hurdles are your own psychological ones, or if there are really external things you can/should be doing to improve your leadership style.  You may want to read a bit about The Imposter Syndrome, which women suffer from much more than men — it’s basically a feeling that you’re a complete fraud and you’ve somehow duped everyone into thinking that you’re competent and capable when REALLY you’re about to lose it all at any minute.  I remember reading about it for the first time when I was 25 and thinking, “by God, there’s a NAME for that feeling?”

I’m curious to see what the readers say here.  Readers, how have you grown your own leadership skills?  Do you look for/appreciate advice specific to women, or do you prefer to hear the same advice men hear?

Reader A thinks her look is too “tomboy” for the office…

I am writing to you in hopes for some advice on how to change from a “tom boy look” to a mid-level executive in a financial institution.

I know that your blog is mostly geared toward New York lawyers, but while I am neither of those (Dallas, Tx – Financial Analyst), I am confident that you can help. A little bit of background…I grew up in a very small town climbing trees and playing with boys. In college, my dress attire was jeans and over-sized T-shirts. It wasn’t until my senior year that I started wearing T-shirts that fit.

Making the transition from college life to financial institution was a little easy back home, (South Texas/Rio Grande Valley), but now that I reside in Dallas, I feel that my current wardrobe isn’t cutting it. My current attire is grey slacks and a button down or simple one-tone blouse. While I mentioned my basic attire, please note that I own about 2 pairs of slacks/dress pants (black and grey) and 2 button downs (purple and maroon).

I have a pair of black shoes and I wear those with black dress socks.

I have never been a “girly-girl” (not that I am opposed to it), but I have always lacked the ability to match colors and styles without looking hideous.

This is a great question, A.  What you’re wearing doesn’t sound so bad to me (albeit a bit boring, but there’s nothing unprofessional about that), but the vibe I’m getting from your email is that you don’t feel elegant, feminine, or sophisticated.  I think it’s important to distinguish unprofessional attire from attire that isn’t elegant/feminine/sophisticated — there have been a lot of very, very successful women who wore nothing but boxy suits, had masculine haircuts, and wore clunky heels (or flats).  In fact, to a lot of older people (both men and women) that is the best way to convey that you’re serious about your job.  (I was just reading a comment on an older post about whether long hair is appropriate — the reader noted that when she ran for office, no one took her seriously until she cut her mid-back-length hair into a Hilary Clinton cut.)  (Pictured: Tomboy Shorts, originally uploaded to Flickr by FredoAlvarez.)

That said — my own attitude (and the ethos behind this blog) has been that today it is possible to walk the line between something feminine and fun, but still be professional.  Sometimes we have debates on what’s appropriate for the office (see today’s TPS); sometimes it really just depends on what’s right for your office.  There are some easy ways to add feminine flair to your outfits, though, that should be pretty safe advice no matter what your office.

1) Add heels. They don’t have to be high; in fact I would recommend starting with what you can walk in.  (You may want to check out our Guide to Comfortable Heels, and the comments there!)  Keep in mind that as you get better in walking in heels, a slightly pointy toe and a skinny heel will be the best way to elongate your legs and make your look more feminine.  How pointy a toe is appropriate is something that changes with fashion — long pointy toes were popular a few years ago (looking back, some almost looked like elf/witch shoes!); nowadays a very slight point is popular.  I would suggest looking online at some of the high-end brands, such as Manolo Blahnik, Christian Louboutin, and Ferragamo, to get an idea of what your ideal shoe right now would be, and then looking in whatever range your budget/walking ability allows.

2) Add jewelry. I’m a big believer in jewelry adding a lot of personality to your outfit.  To start small, you may want to get a good set of fake pearls to try out how those feel with your button-downs and t-shirts.  (You can always invest in a better set from Mikimoto or even your local jewelry store later on.)  Similarly: what watch are you wearing?  If you’re wearing a sporty watch, this might be a good time to investigate how a more feminine watch might feel, either with a leather strap or a metal strap.  Earrings are the third “start small” piece that  I’d recommend.  Personally, I hate posts, but I feel like dangly earrings are inappropriate for many offices (and distracting if you move your head a lot) so to me the perfect office earring is the “huggie,” so named because they’re hoops so small that they hug your ears.

3) If you’re not already wearing makeup, add some. It doesn’t have to be a lot — sometimes just a lipgloss with a slight tint is enough for women.  (It’s a bit too light for me, but a number of friends love Fresh Sugar Plum Lip Treatment SPF 15, or I’ve written before of my love for CoverGirl Lipslicks. Clinique Almost Lipstick is another classic.)  Have a good friend help you with this if you’re really clueless — how does your face look right now?  For me, I know I look a lot prettier when I add concealer under my eyes, curl my eyelashes, and add a bit of blush and a bit of color to my lips — I generally don’t leave the house without those. For work I also wear mascara, eyebrow pencil, eyeliner, lip liner, and lipstick; for nights out I’ll wear 3-5 different shades of eye shadow as well as a few more coats of mascara; I’ll also use a highlighter like Touche Eclat or wear a sparklier blush, like NARS The Multiple Orgasm.  My point here is that makeup is not an all or nothing proposition — it’s a continuum, and even just wearing a little bit can help you look and feel more feminine.

4) Find inspiration in a celebrity or public figure (anyone who’s photographed often), or even a character on television.  I would recommend looking for someone with your body type to get the most out of this exercise.  Take note of what she wears — how does the fit of her clothes differ from yours?  Is there a color combo that she wears that you could try?  How about her jewelry and shoes — can you add more personality to your outfit that way?  Another option here would be to find a few static photos of this celebrity/character that you really love — I would say 6-10 photos — and visit a personal shopper (such as one at your local department store), or even a personal stylist.  For my $.02, I think it’s important that you go in with an idea of what you want to achieve before you meet with them, but maybe that’s just me.

Readers, what are your best tips to add femininity to the professional wardrobe?  What do you think about Reader A’s question?