How to manage your image


My mother always told me, “Dress for the job above yours. No one will give you a promotion until they can imagine you in the higher position.” So when I worked at 31 Flavors in high school, I didn’t wear a baseball cap like the other scoopers. I wore a crinkly, white paper hat, with brown and pink polka-dots, because that’s what the manager wore.

For a while, what I should wear was clear. In college, when I wanted to be David Kramer’s girlfriend, I wore soft blue sweaters like his fiancé. At my first real job, I was “the Internet person” at a Fortune 500 company where everyone wore suits and I wore jeans because that’s what the guy who ran Netscape wore.

At some point, though, I got stuck. At some point between middle management and top management, I couldn’t find anyone to dress like. I rarely made deals with women and I rarely encountered a woman as I bounced between investors. When I did encounter a woman at my level, she wore a suit, or a least a jacket, which would not be appropriate at my own scrappy startup.

I wanted to wear clothes that would make me feel appropriate in a crowd of 20-year-old programmers and a crowd of 50-year-old venture capitalists. I noticed that khakis and a blue shirt do the job for men: The hip black shoes fit in with the programmers and the expensiveness of the shirt fits with the over-fifties. But khakis and a blue shirt on a woman screams, No style and probably boring — especially if she wears it as many days in a row as the men do. It’s a double-standard, but it persists, and probably-boring is not a trait people want in a leader.

So I hired a stylist. I hired one who dresses sets for sitcoms. But if someone’s sick she dresses the people. I tried to focus on the people instead of the props and that made me trust her. Her name was Allison. She looked at me as her big break into the high tech industry.

She took me to Nieman-Marcus and told me next time to dress nicer so we get better service. I tucked my T-shirt into my jeans. “Forget it,” she said. She said shoes are most important and my eight pairs of black loafers are not stylish. “Glamour is in,” she said, and she picked out shoes I would never choose.

I thought about the time the dentist told me about his business plan and when he took his fingers out of my mouth I told him ten companies already did that, and he didn’t believe me, and I thought he was a fool for not trusting an expert. So I tried to trust Allison.

The shoe salesman knew Allison was special. She knew the shoes he had in back. She knew the colors designers favored and said, “Don’t bother with brown from Chanel.”

I tried on Fantini heels and teetered. Allison said, “You look beautiful. Can you walk?”

I said no.

She said try.

I teetered.

She said, “You walk fine.”

I said, “There can’t be a hint of teeter because people already subconsciously think women aren’t sturdy enough to run a company.”

Allison sifted though shoes for lower heels.

The shoe salesman said, “But you don’t want the men to think you’re a prude.”

I looked at him. I looked for signs that he was scum. I don’t know what I was looking for. I was looking for a reason to scream at him. But he looked so young and innocent. Maybe this was his ice cream scooping job. I said, “Would you say that to a man who was buying shoes for work?”

He said, “A man would never buy heels.”

Allison looked up at me and gave me a sort of it’s-not-worth-it look.

But I persisted until he said, “You’re right,” in a way that meant, please buy shoes from me. He said, “I’m really sorry for offending you,” which meant, women are so volatile, I wish I were in the tie department.

I said, “Thank you,” which really meant, I am so gracious and you are ignorant and you will marry a woman with no self-esteem so that you do not have to notice your own shortcomings.

Allison hustled me through each department. She taught me rules of thumb: DKNY and Tahari are casual but sophisticated and that’s the look that lies between dinky startup and Fortune 500. I told the Mac makeup artist that I am a high-tech executive and I need to look a little older than I am. He told me to buy bright red lipstick and black-rimmed glasses. “Even if you can see,” he said. Allison concurred.

I unveiled my new look slowly at work. Lipstick one week. Glasses the next. Shoes on days I’d be sitting. I noticed as my wardrobe changed, the women who reported to me changed their wardrobes. Like my mom called them up or something. I tried not to think that Allison and I were making my office look like a sitcom.

Soon I started taking my appearance more seriously. And I ditched the glasses because I didn’t want any woman reporting to me to think she needed glasses even though she could already see.

39 replies
  1. Anonymous
    Anonymous says:

    I loved the post. Except, here’s one for you: what if the person a level or two above you (and your boss) dresses poorly?

    My relatively new boss is very senior at a large financial serivces firm and doesn’t dress that stylishly.

    It’s not that she dresses badly, it just often looks like she’s wearing something that hasn’t been in style for a decade or it’s something that doesn’t really fit her properly (ie pants with hemns too short) or colours and patterns that don’t flatter her and seem out of place (and style).

    Would you recommend emulating her style?

    My gut feeling is no. I should continue to dress the best way I know how for a woman who needs others to trust what she says and make multi-million dollar decisions based partially on what she says.

    The boss’s executive assistant dresses very fashionably and professionally, so I know the boss is okay with other women “out shining” her in appearance.

    Any thoughts?

    (Obviously fashion didn’t matter that much to her career as she is a star in a male-dominated field.)

  2. Chris Yeh
    Chris Yeh says:

    For the umpteenth time, I’m glad I was born male. All I have to worry about in the morning is whether to go with light blue, dark blue, or French blue, light, medium, or dark khaki, and brown or black belt and shoes.

  3. annaigart
    annaigart says:

    I loved this one.
    I appreciate this line particularly:
    “I tried not to think that Allison and I were making my office look like a sitcom.”
    Thank you for your posts, Penelope.
    Lots of luck with the book!
    Would you post a link to it when it is available?

  4. Diana
    Diana says:

    Another great post! I can really relate to your stories, but this one so particularly! Great move hiring a stylist, I think. Am I wrong or isn’t there a whole industry of “image consultants” now who work in a similar capacity? I remember you mentioning something about that in a prior post.

    I happen to work in one of those dreadful “business casual” offices where 99% of the women there dress as casually as they think they can get away with (floor-length elastic-waist knit skirts, sweaters two sizes too big, poorly-fitted courdoroys, loafers, white socks, cotton turtlenecks, etc., etc.). I think I’m one of the only women there who pushes the *upper* limit of what defines business casual. I stop just short of wearing a power-suit… I pick out nice trousers, pencil skirts, button-up shirts, sweaters that actually fit, etc. I tend to wear flats or low (2″ max.) heels, because I think it makes me seem a little bit more approachable and practical. I think wearing sky-high heels would make me seem like I was trying to show off or impress people with my vanity. Essentially, I am trying to appear young, bright, fresh, and confidant. I just started working there, so I can’t really speak to whether my wardrobe strategy has actually improved my chances of a promotion/raise/honors, but I have received a lot of positive feedback about my work so far, that I’m a quick-learner, adaptive, creative, etc. and I think at least a part of that impression comes from the fact that I stand out from my coworkers who for the most part look like they rolled out of bed and are still half-asleep. I have noticed at least on co-worker stepping up her wardrobe after the first week of my working there, but I can’t say whether that change was due to me or some external force.

    I think some women might be hesitant to step out of the norm of what “everyone else” is wearing, but if you can it really showcases your confidance and positive self-esteem (even if, like me, you wish you had more of both!). Some women might say that how you dress at work doesn’t matter, espcially if one doesn’t have to interact with customers. My response? You interact with you boss, and they are responsible for promoting you or firing you, so dressing professionally shows them respect as well as showing them that you care enough about work that you’re willing to put a little more effort into your appearance.

  5. Miriam
    Miriam says:

    How’s this for image constraints – I run a business that provides quality English content to Israeli businesses. Here’s the catch – I’m a religiously observant married woman, which means that I dress quite differently than all the secular (mostly men!) people that I work with – I wear a headscarf or hat, and I only wear skirts, and shirts with sleeves. I dress as professionally as I can within those constraints, but it can be quite shocking for people to realize they’ve been in touch with some religious woman. At first I was worried about the impression that I would make on people, and that I would lose business as a result. But I decided that this is who I am, and if they realize I’m professional and nice to deal with, it will be hopefully be ok.

    And it has been surprisingly more than ok. I can see that for the first minute or two when people meet me in person, they are often taken aback, but once we start talking they soften up, and even hire me and recommend me to others! One company rep even told me that she was shocked when she met me, but once we started talking she could see that I was professional and would provide a good service.

    Appearance is important, but you also have to be yourself – you can’t escape who you are. Smile, be friendly, nice, and be genuinely interested in what others do and what they need. My experience has shown that people mostly don’t judge a book by its cover, which is certainly lucky for me!

  6. PunditMom
    PunditMom says:

    I love this story, Penelope, especially your comment to the shoe salesman about whether he’d say to a man that he should worry about looking like a prude.

    I believe I had the “right” clothes when I was in broadcasting, law and public affairs (especially the shoes!)

    But now, as a freelancer (correction: professional writer!), I work from a home office after dropping off my daughter at school each day. Some days it’s jeans and some days it’s yoga pants (I like calling them that better than sweats!). But I’ve been wondering lately if I need to change my attire, even though there are no co-workers in this little third-floor office, so my professional self image can be boosted a little?

    Would that change my mindset about what I’m writing and who I’m writing for? Or would it just be an excuse for more shopping?

    I know that part of how I felt in the office setting was, on many days, somehow related to whether I tbought my attire sent the message that, “I’m smart and competent.”

    What do my yoga pants say about me now?

  7. Penelope Trunk
    Penelope Trunk says:

    Chris, Thanks for laying out the choice of blues so clearly. Who knew?

    Diana, Thanks for the great explanation of why you shouldn’t wear your gym clothes to the office.

    Miriam, Thanks for bringing up the diversity issue — it’s something that’s really important to me to talk about on the blog. Sidenote: In New York City I was so completely out-styled by the Orthodox moms at my son’s school that I found myself emulating their look.

    Anonymous, just because your boss has shortcomings doesn’t mean you should emulate them. Each of us has stuff that is holding us back and we have to fix it. Your boss undermines her leadership by looking poorly put together. Don’t emulate that. Maybe she’ll learn a bit from you in this department and she’ll be grateful.

  8. Dave
    Dave says:

    My biggest wardrobe challenge these days is figuring out how to change out of khakis and back into jeans before people find out I had an interview! And wearing shoes that can work in both situations.

    I agree, women have a rough time of it, especially in technology companies. For guys, it’s usually more about how not to overdress; the better the clothes, the lower the perceived technical competence level. I recall one time I wore a blazer to a sales call at WebTV and they didn’t believe I was an engineer. Khaki + polo shirt = senior engineer on a sales call. Khaki + collar shirt + blazer = sales engineer. Tie = consultant.

    Suit? Um, suit = “suit” = I don’t know…a narc, maybe? You’ll have engineers saying stuff like “Who brought Five-O to the meeting?”

    • Alisa
      Alisa says:

      Dave, great comment about nicer clothes and perceived technical competence level. I’m not a strictly speaking technical person, but I often work with technical people (I do UX research, and am finishing my graduate work in HCI). For me it has come down to two wardrobes: blazers and slacks for presentations and client-facing days, jeans and witty tshirts for days with the development team.

  9. Heather Mundell
    Heather Mundell says:

    Your mom and my mom must have gone to school together!

    It was 1988, and my mom couldn’t wait to take me shopping for grown up work clothes for my first interviews. She was all about dressing for the job you want. I therefore ended the shopping trip possessing the wardrobe of a 48 year-old, but I thought that’s what I was supposed to look like.

    I was usually the youngest wherever I was working and I’ve always looked younger than I am (that used to stink, but now it’s really great), so throughout my HR career I was dressing not only like my boss, but like a grown up so people would think something like, “She looks 13, but what 13 year-old would wear that suit?”

    Now I work from home and have a small collection of “professional clothes”, all of which I really like. If I lived in NYC or San Francisco or really anyplace other than Seattle, the Casual Capital of the universe, my professional clothes would probably look a lot spendier and less comfortable. It’s all about blending your personal style in with the context and hoping you’re not way off base.

    Loved your post! Laughing while I read has been a highlight of my day.

  10. Will
    Will says:

    About the guy at the shoestore. Sounds like you are only able to take advice from an expert when it serves your ego. What’s the point of advice if your ego can’t handle it? I guess your reaction proves he was right about you being prudish. A non-prude would just have had a good laugh and moved on. Cheers! :)

  11. scarlettholly
    scarlettholly says:

    I work for a female CIO for a huge corporation, and she very distinctly works her own, feminine style. I have only ever seen her in trousers once, and that was a day that she had absoltuely no meetings.From her I have learnt that sometimes emphasising your femininity in a male-dominated environment isn’t necessarily going to hold you back. Plus, it gives me an excuse to wear dresses to work.

  12. P.O.'d
    P.O.'d says:

    “I said, "Thank you," which really meant, I am so gracious and you are ignorant and you will marry a woman with no self-esteem so that you do not have to notice your own shortcomings.”

    I particularly enjoyed that little thought…way to let your true colors shine through Penelope. You’re a great example to us all.

    *End of sarcasm*

  13. Patricia Foster
    Patricia Foster says:

    This is an interesting discussion.

    I wish I could wear really sophisticated clothing to work. While nothing is actually stopping me from wearing a power suit, I work in a university library so there are times that I really do have to kneal down on the floor to do things and physical labour to boot. And being on my feet all day with ankle problems is a shoe issue. It’s not easy to dress “above” but I usually do dressy casual (the mexx look)instead as the clothes are more durable. However, most of my co-workers dress like they’re on a 1970s camping trip. I consider that too casual for the kind of work we do.

  14. Chris
    Chris says:

    Will and P.O.’d: Doesn’t your irritation over her irratation make you, I dunno, worse than her? I mean, you weren’t able to keep from telling her about it, whereas she at least refrained from venting until she was able to blog.

    On the one hand, I think it’s entirely likely that the shoe salesman had a point about the implications of certain shoes (not that lower heels make you appear prudish, but higher ones do tend to give a more feminine impression). On the other hand, it’s got to be irritating to have to live in the sort of world that’s always pressuring you to be rather… unprudish.

  15. Kelly
    Kelly says:

    This idea is great in theory but not very realistic. I have a good paying job but I can’t afford to dress a step above and most people I know can’t afford to dress a step above. I barely afford my professional edge as it is. This is real life, people have bills, house payments, kids, car payments, etc. I believe in dressing well but I think that this article is sort of disillusioned.

  16. robin / koda
    robin / koda says:

    Chris-you don’t need to spend a lot of money to dress nicely.

    I am in a position like annaigart: “I happen to work in one of those dreadful "business casual" offices where 99% of the women there dress as casually as they think they can get away with (floor-length elastic-waist knit skirts, sweaters two sizes too big, poorly-fitted courdoroys, loafers, white socks, cotton turtlenecks, etc., etc.). I think I'm one of the only women there who pushes the *upper* limit of what defines business casual.”

  17. Mary
    Mary says:

    Interesting but what would your advice be to a woman who didn’t have any desire to climb a corporate ladder? Is she free to dreass how she likes?
    * * * * * *
    Everyone — male or female — needs to pay attention to the image they project. We all want something in life, we each have goals. How well we align our image with our goals affects how successful we are at reaching our goals.

    Here’s another post about that:


  18. Gaby
    Gaby says:

    I agree 100%. I’ve always wanted to hire an image consultant, but don’t know where to find one in my area. I would appreciate anyone’s comments

    ** * * *

    Good question. This seems like a good place to start looking:


  19. Ayo Fashola
    Ayo Fashola says:

    As an entrepreneur and image consultant, it’s important how we present ourselves. No one is saying to be a fashion victim, but look like you care. Look like whoever you say you are. If you say you are a creative, smart, intelligent, and a successful writer, artist, musician, IT, then looking the part won’t hurt. We do not want to hear you say it. We want to see it. We make judgements all the time about others and you definitly do not want your appearance to be the reason why you do not get whatever it is you want in life. You may not be able to control what others think of you, but you can control what you project and there are no excuses. Bills, mortgage and kids are not excuse to look less than 100% Your attitude about your work, and whether your ideas are current and up to date will be reflected in your personal appearance. If dark wash jeans are in to convey comfort yet professionalism and you show up at a client meeting with light colored jeans that do not flatter your figure, you are not current in your ideas. Your style, your appearance, your grooming matters if not more than half than your “hard work”

  20. En Vogue Styling
    En Vogue Styling says:

    Interesting blog and excuse me, I just perused it slightly. As a fashion stylist who also works as an image consultant, I will say you can never make a second impression. So yes as people will judge you within 5 seconds of seeing you, it’s imperative to always look your best….be it casual or formal. You never know when you will look into the eyes of your next boss, significant other or someone else of great consequence in your life when you are just rushing out the door in your torn up sweats for a carton of milk. Remember too that image is about your body language, mannerisms, the words that come out of your mouth, and your attitude that is either cheerful, elitist, off-putting, or graceful. There is only one you so take the power in your hands to the best you you can be.

  21. Randy
    Randy says:

    It seems to me that you are trying to be taken seriously, that is good. It also occurs to me that you are acting more like a man does in being confrontational with the shoe boy. You want a double standard it seems because you want one thing and act another way to meet your objectives. What you want is to be taken seriously, yet you turn right around and fall prey to the very thing you despise. Odd.

  22. Judith Rasband
    Judith Rasband says:

    As an image consultant, I always tell people when in doubt, dress in an unmatched suit — suit jacket and unmatched slacks or skirt (for women) on the bottom. If you arrive at a business event and feel too overdressed, you can always take off your tie or jacket to feel more approachable and casual.

  23. Jonha
    Jonha says:

    Hi Penelope,

    I’m sure wardrobe is the last problem in your mind that you’d ever want to face. I just feel it, because I also do. I think I won’t have as much problem as you did because anyone could teach me how to walk and I would. Anyone,maybe especially if someone like Allison would teach me the makeup essentials and I would remember. But then again, I might rather end up wearing sweatshirts than those expensive dresses they expect you to wear.


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