Fashion Undressed: Executive Style

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alison santighian for wardrobe oxygen

I never consider my age in my wardrobe. I sit squarely in the “if you love it, work it” camp. For heaven’s sake, I own and wear a peach crop top with a crocheted elephant. Heck, I never consider my age in anything. I have to pause when I’m in conversation and make a Seinfeld or Friends reference, and I get a blank stare, and then realize the person across from me isn’t old enough to have watched those shows religiously. My age just isn’t part of how I choose to dress, whether for weekends or for work. I’ve been fortunate to work in roles that, while certainly not in the “creative-wear-what-you-feel” realm, and are even in the conservative camp (my last company was an accounting firm), I can push the envelope. I have no issue being the one in the lava colored “powerpants.” Ever.

I thought carefully when I picked out the clothes I wore last Friday, and the ones I put on this Friday. I thought twice when I tried on a dress I ordered so I’d have an easy, professional go-to in my closet, and it was just a bit shorter than I like to wear in the office. I checked the mirror again when I put on a dress that should be a reliable knock-’em-dead standby, but it hugged my body with at least five pounds more force than it did a year ago.


I considered a lot when I went to buy a few new pieces for my closet because I have a new role in my career. Because I love clothing and fashion, choosing them should have been a small joy. Clicking through the spring sales should have been a celebration of my professional accomplishments. Normally, it all would be.

Over the last month my clothing choices felt weightier. Though I’ve been in similar positions for the better part of 10 years, this new one is unabashedly, formally executive. That label seems to have effected me sartorially, and I’m off kilter. As I get dressed each day, I’ve noticed I shy away from things I used to wear easily: a sheer top I’d wear with a camisole and balance with conservative trousers, a dress I bought (and love) that’s about half an inch shorter than I’d like, or stepping into higher heels with a skirt for fear the hoochy factor would go too high.

That last one, especially? It blew my mind.

I have absolutely no issue with using what I’ve got at my disposal. I’m a tall, well-proportioned, and fit woman with an unusual haircolor and strong, shapely legs. I know my appearance can be powerful. If I have a major meeting or presentation, I turn to my snakeskin and vibrantly colored sheath dresses. I put on my Stuart Weitzman pumps. I add rhinestones to my ears and wrists. I put nothing on to distract, mind you, but I know what works.

So why am I hesitant, all of a sudden, to use the tools and armor on which I’ve relied for years, and, quite frankly, push women around me (of course you can pull off the print mixing and the unusual heels or the blouse with the progressive cut, go for it!) – all because of a formal role shift? I’ve been mulling over the phenomenon probably way more than it warrants. It’s stuck in my craw, so I’m going to wonder out loud.

Putting this out into cyberspace is scary. I’ve known many of my colleagues for years, but some don’t know me at all. That fear aside, I suspect there are other women out there wondering and thinking the same things, so here we go.

So far, the most significant reason I can find for my hesitancy is that I don’t quite believe that I’m an executive, and part of a team making decisions for the strategic direction of a company.

There. I said it. I can’t imagine I’m not the only woman to share this insecurity out loud. Sure, maybe there are men out there with doubts; those doubts show up differently for them, I’d think. For me, it’s showing up most clearly in my clothing choices. I’m hesitant to wear the strong things I wore not 2 months ago because I don’t trust my own abilities.

Daily, I remind myself to not couch my opinions with conditional phrases. Daily, I bite my own tongue to cut off the modifiers to hedge my statements and proposals, both virtually and literally, so I do say I mean. Daily, I push forward in areas new to me, just beyond my comfortable expertise, and hope that no one sees through me. Daily, I stop and think twice before I ask a question, for fear someone will interpret that question to mean that I don’t know my job.

As an accomplished 41 year old, it seems incongruous to me that I feel this tentative. I feel silly worrying about my clothes. I’m ashamed that I don’t believe outright in my abilities and capabilities. If they even notice it, those around me don’t see my clothing other than as acceptable. Rather they see me as able, capable, and strong.

I wish I could say writing this, getting it off my chest, is helping me work through it. I hope it will. At the moment, though, I’m still feeling tentative and wary. So I’ll just bundle it up and use it. I’ll coach myself through those timid moments. I’ll put on my Big Girl Panties, hike them up high, and march forward. I’ll remind myself that I can use clothing as armor, as strength, and if I need it, it’s there. But more than any of it, and pardon the Stuart Smalley moment, but I’m strong, I’m able, and I kick ass. And gosh darn it, people know that.

I put clothes on daily, and I love the challenges I’m conquering in my role. Each moment holds some confidence and a dash of fear. I’ve decided that’s the way I want it right now. I don’t have the answer as to how to feel as strong and capable as others see me and as I know I am, nor do I know what any of this means for my closet, if anything. I’m going to keep thinking and writing about it over on my site under the tag “Executive Style.” If you’d like to join the conversation, I’d love to have you.

Alison SantighianBy day, Alison Santighian is a contractor for the federal government, using her super powers to serve our country, but by night (after bedtime for her “Beans” now 7 and almost 5), she pines after the “it” factor. Alison and “H” (better known as #besthusbandever) don’t believe badass has an expiration date, so they hit concerts, shows, restaurants, and openings across the globe. Alison also writes for Glass Magazine, adding a business woman's eye to fashion week reviews and style features. Follow her on Twitter.


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  1. “I never consider my age in my wardrobe. I sit squarely
    in the ‘if you love it, work it’ camp.”

    Thank you! I feel the same way and regularly receive compliments on my style. I wish more women could enjoy this feeling.

    I have never faced what you’re going through, but I hope you can kick your kick your wardrobe insecurities (and any other related insecurities) in the ass soon!

    1. Sisters! I get the same compliments. Thank you for this great reminder – it helps remind me of how strong I can feel – and how much I love kicking ass!

  2. This really gets to me. Last year, I went from one job at a company where I had been for over fourteen years as a worker bee to a new job at a different company as a team lead. On the one hand, the dress code is business casual and the only person who wears a suit is the program manager. I want to dress well for my new job but I don’t have an outward facing role and I spend all day in front of a computer in a cold office.

    1. It’s an odd shift, isn’t it? Congratulations on the new role! So marvelous.

      I love business casual because there’s so much leeway in it. That being said, if the PM wears a suit, it’s worth wondering if you should follow the example in some understated way. For example, there are so many great jackets out there that will elevate a simple look quickly, and would be perfect for a team lead (I’ve been converted to DC Style Factory’s eternal recommendation of a white blazer – so crazy versatile – check her out online, or holler, and I can share a link).

      1. I’ll definitely check it out. A blazer wouldn’t be out of place there since I’m always cold in the office.

  3. I loved this piece. I work in a heavily male dominated field (sometimes I’m the only woman in a room of 100), and the further I progress in my career (and frankly age), the harder it is to decide how to dress. I never know how to respond when one of the guys tells me “you look so pretty” or worse yet, when I’m introduced on stage as the “pretty one from the office” (an easy designation since I’m the only female). I know it’s all said with the best of intentions, but it feels like I’m being judged on how I look as opposed to the work I do. I often wonder if I’m making it worse by wearing feminine clothing. I would describe my style as pretty conservative, but I wear a lot of skirts and I love a good pair of heels. However, I’m finding myself shying away from these choices when I know I’m kicking off a training event and I’ll be on stage introducing the speaker and making opening remarks. And it’s all complicated by the fact that as I get older (I’m 43), I worry more about aging and not being considered attractive. I tell myself that I shouldn’t care about what others think of how I dress or age, but honestly, I do care how others perceive me. And I think the perception of others has a direct impact on my career.

    1. Jenny, your thoughts are so similar to my wonderings. Oddly, I’ve found that, as long as I keep it reasonable (and that’s part of our dilemma, isn’t it?), I do better and feel better, stronger, if I use the strong but still feminine pieces I love when I’m kicking off events or meetings. I want to be remembered, but also wonder if I’m remembered for just those reasons you name: because I’m the woman/girl. I also wonder whether it matters why they remember me, as long as they do. I can wow them with my skills whenever I interact with them.

  4. In Principles of Psychology, William James writes that clothing is second only to the body in understanding his or herself, categorizing clothing along with the spirit and body. I find clothing to be a kind of complement to a given mental state, helping accentuate whichever part of my personality I need to in various situations. Perhaps your hesitancy to dress as you did before is because you have a different mental notion of what an “executive” looks like. Perhaps your old wardrobe speaks to your old job, your old responsibilities, and maybe dressing more conservatively fits this persona, right now. Or, perhaps because you have to recreate your sartorial identity at the new job, you are protecting yourself from conservative, chauvinist ideas others may have of anything worn not purchased at Ann Taylor. If that’s the case, it seems kind of natural, and as people know you, you’ll feel more comfortable expressing yourself more flamboyantly.

    I know for me, in the last 7 years teaching, my style has gone from pretty Ms. Frizzle-inspired, with a lot of feminine silhouettes and some frill, to pretty androgynous styles in neutral colors. For me, I’ve found that though I can wear brighter things (and I suppose similarly am somewhat tall, with red hair, and some new muscles I love to show off), I don’t need to, and don’t want to a lot of the time; I guess my point is as I’ve become more confident in my role, I express myself less. I absolutely love creating my work outfits, but in the end, I love my work more. I’ve started to feel like if I dress more simply (I mean, Helmut Lang/Rag and Bone simply, not I’ve-given-up simply), my ideas and my presence won’t have to compete with a printed top with hand-painted raccoons on it. And funny enough, before, when I was overweight, I wore detailed pieces like the aforementioned precisely to distract from my weight. I kind of love the confidence it takes to create a really well-curated, simple outfit, letting great hair, or a good lipstick, stand out.

    Since I am about to have a big career jump in this next year, I’m thinking a lot about how I want to present myself, and I love that you’re so cognizant of these kinds of nuances.

    1. chiefbeasty, just seeing your “handle” made me smile so much. You’ve hit a couple of nails on the head, particularly that about comfort and confidence levels tying to an ability to express oneself more or less. My question to you is one that came up for me from a comment on the Wardrobe Oxygen facebook page post for this piece: Is your shift to the Helmut Lang/Rag and Bone simple because of your comfort level in your role or because of your age? I do, of course, realize that they’re likely tied inextricably.

  5. Alison,

    I’m older than you by quite a bit and I never have gotten over feeling like a fraud. The right clothes do help somewhat, but even wearing those, I feel like I am in drag. To make things worse, although I am tall, I am not good looking like you. Since I have little to no support from how I look, I feel like I have to work harder than everyone else to be “acceptable”.

    In spite of my misgivings, colleagues ask me to speak and write. Somehow, they think what I have to say is valuable. But inside? I am a wreck. I do have to say that Allie here at Wardrobe Oxygen has helped me to dress better, so at least I’m improving in that regard.

    For some reason, people think they can confide in me. I am surprised how many of them have that familiar feeling of, “I’m going to be found out at any moment and then it all will be over.” Mostly I have heard this from women, but some men too.

    My first reaction is to think that if were as gorgeous as you, I would feel confident and happy all the time. Yet I know better. It’s not that simple.


    1. Chris, thank you so much for this. You’re right, it’s not that simple. We all bring loads of baggage to the table about our appearances (for example, my perception of my appearance is drastically different than yours of me).

      As I wrote the piece, I was certain that, no matter how afraid I felt about “revealing” it, there were others – many others – who felt the same. I’ve heard similar from friends and colleagues, both male and female. Like what you’ve heard, though, people are afraid to open up about it. I wonder if our very visible, online society has anything to do with it (says the writer active on social media and whose publishing platform is the internet). We see these “be strong,” “be your dreams” platitudes and they somehow convince us that we have to be more than we feel – without feeling like the fraud we do.

      That you have the honor and the graceful power of earning people’s trust is a beautiful thing.

  6. This post really resonated with me. I am in the process of moving into a more prominent, higher status position in my office, I am also 41, and I have started to second guess some of my own more whimsical choices in office wear. Even on weekends. People ask often enough what I do, and where everyone is a potential client/referral source, I have to always think a bit more of the impression I make in terms of being responsible and trustworthy, and a good representative of my company, while still being true to my creative, whimsical self. It’s a tricky line to walk. Thank you for this piece that so perfectly captures the dilemma. No need to have all the answers — it is very helpful just to see the questions well-framed, and to realize that, subconsciously, it is something I have been wrestling with too.

    1. I’m so happy that this resonated with you. It’s a very odd place to be in – especially when, as much as we love clothing (and I assume you do because you say your choices are whimsical), we don’t want to believe that it’s as important as it feels in those moments when we can’t decide whether to put on the edgier piece of jewelry over pearls. Though I adore my pearls, I much prefer my
      Shield & Honor rimfire chain earrings and sparkly paste ear candy :-), and wear *those* daily instead of the pearls.

      Best of luck in your new role! The fact that you’re considering it so carefully say you’ll rock it!

  7. The upper level of the workplace are not always friendly to women and your coworkers aren’t always ready to see you in an non-sexist light, particularly if they’d like to get rid of you for whatever reason. Tweaking your work style to keep the focus on what your authority and not on your backside isn’t a personal style cop-out, it’s a move to integrate your aspirations with your reality.

    Contractors who meet with Federal clients need to be a bit bland. If you’re too sexy they won’t take you seriously, if you’re too opulent they’ll imagine you’re making tons more money than they make and resent you.

    You can take those figure-hugging clothes with you on your next vacation, financed by a new salary 🙂

    1. Ginger, it’s interesting what you say on coworkers. I have the advantage here of not knowing most of my new coworkers, and therefore the “space” to reinvent myself, if I feel I need to go that route. The situation might be different if I were still at the company where I “grew up,” and where people still know me as the first role I held with that company or organization.

      That being said, I’m not particularly concerned about wearing figure hugging clothes – I’m probably well on the conservative side of that bent (if I’m tugging at it at ALL, I won’t wear it), and am lucky to have a “this is too tight, isn’t it?” honest judge in my husband (provided I’m not leaving for the office at 0-dark-30).

      I do wear different ensembles based on meetings and activities. Most of the outfits in the collage, for example, are in-office days with only internal meetings, if any. For client or teaming partner meetings, I do – and always have – tended towards a classic, if not conservative choice, and adding a pair of sparkly but not crazy earrings or some other such detail to keep me smiling. I *did* start in the lobbying business, after all. Talk about conservative!

  8. Alison, you have written a powerful piece here. Thanks for sharing so honestly. These are similar to the kinds of questions I have been wrestling with in the last year when I went from being a classroom teacher to the faculty administrator at my school. It is amazing how what we wear can contribute–or detract from–how we feel our inner power.

    1. Thank you so much, Linda. It means a lot that you heard the essence of my thought process: that the clothing is somehow part of how we, ourselves, FEEL and experience our own inner power. I suspect that some folks will read this and hear that it’s about how others perceive us. True, that’s part of it, but only in as much as how much we allow that to drive us.

      I hear your struggle, too, very clearly. My mother went from teacher to administrator (assistant principal) after a long classroom career. She drove my stepfather crazy with her clothing sprees. I think he knew, though, that it was as much about her finding her way and footing in her new role as it was about the clothes. I’m curious to know what sorts of choices you’ve made, though!

      1. Let’s see, the choices I made. . . This year I have enjoyed wearing things that were not practical for a long day of standing and actively moving in the classroom and on the playground–some heels (not every day though!) and pencil skirts. Part of my newer sartorial choices have not as much to do with the job change as just being ready for something different than the eclectic/artistic, colorful, boho/feminine style I have loved for so many years. Now I am finding myself drawn to neutrals, masculine-inspired styles, and elements that have a bit more of a hard edge. I see how this does fit into my new role somehow, which is adult-focused rather than child-centered. However, there are many days I am happy to revert to dressing just as I used to. Because I work in a creative kind of school (hurray for Waldorf!) I have a lot of latitude.

        1. Interesting how much your description aligns with what another reader, chiefbeasty (below), says has happened to her wardrobe as she’s grown in her education career (albeit higher ed). I also find the child- v. adult-centric perception astute. Thanks so much for sharing these!

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