The Tomboy in the Suit

how to avoid looking masculineReader 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?

Share on FacebookTweet about this on TwitterShare on LinkedInShare on Google+Pin on Pinterest


  1. Do “we” still believe that a professional woman must wear a jacket — or jacket equivalent — to be taken seriously?

    FWIW: I do believe this. But I’m wondering what the general consensus is.

    • I think it depends. If men are wearing suits, women should be wearing jackets too. It looks so unprofessional when you go to a meeting and all the men are in suits and there are women wearing sleeveless dresses or slouchy cardigans. But in a business casual environment, then no, a jacket’s not necessary.

      • I work in a casual office setting and am business casual in front of my clients. I do find that a third piece, whether it’s a jacket or a cardigan, does look more polished and put together.

        • Depends on your profession. If you’re in a jacket-wearing profession, then you need a jacket. Otherwise, you don’t.
          That being said, I think a jacket always looks more polished than a cardigan. Sadly, for my line of work, a jacket would be way too much.

  2. Fictional Wardrobes As Guidance :

    Does anyone know if there is a website that publishes the wardrobe details of film and TV characters? I’m thinking of the wardrobes of Vera Farmiga in “Up In The Air” and Julianna Margulies in “The Good Wife.”

    • The costume designer for the good wife has a blog where he details lots of wardrobe things from the show:

    • Corporette used to!

    • I was just watching “Fair Game” tonight, and thinking how much I liked Naomi Watt’s wardrobe as Valerie Plame.

      • The wardrobe guy for Kyra Sedgwick has a good blog on the website for The Closer.

  3. Aside from adding some light make up and some cute jewelry, I think she should make sure to pick up some tops/blouses in some lighter, more girly colors. Pale pinks are usually easy. If she gets a friend whose opinion she trusts, even a floral or small cutely patterened blouse could go a long way.

  4. better fit (tailoring, better fabrics (higher end) and drape, and accessories. silk scarves can add an element of polish and style to otherwise very dull outfits, very executive looking in my view.
    …and never being inappropriate- ie too much skin or too tight.

  5. Anne Shirley :

    You have 2 button down shirts now right? I’d add a sweater or 2 – cotton for summer, but good with A/C. A 3/4 length sleeve perhaps.

    I don’t think you need to go more feminine, but just a shirt + pants doesn’t look “finished” to me. I’d stick with those shapes, if you like them but try to add something extra every day- sweater, fun necklace, cute shoes, belt, etc. And make sure the rest of you is finished- no wet hair to work etc.

  6. Invest in a good quality bag, maybe a satchel type that could also hold documents in a pinch.

    The devil’s in the details–it’s adding a scarf, a piece of jewelry, It’s checking your outfit for proper fit, but it is also making sure all your buttons are on, loose threads are snipped, no stains–and for heaven’s sake, iron your clothes or have them professionally done. Be sure your nails are manicured–not necessarily polished, but clipped, clean. Shoes-polish them and check for heels that are “running down”-get them to the shoe repair shop, or discard altogether.

    When you purchase something new, be sure it will mix/match well with what’s already in your closet–it gives you more variety when you put an outfit together. Most of my work wardrobe is composed of separates for this reason.

  7. I agree with the feminine v. professional and Nordstrom shopper points above, but I wanted to highlight the ease of a well tailored suit for people who find it hard to match things on their own. The best way to look more professional is to wear a jacket that fits, whether it is over a dress or part of a suit. Get to know the lady in your dry cleaners who does tailoring. They are life savers.

  8. I know from experience that it can be hard for us short curvy girls to find the right fit in professional wear. Big boobs mean you have to upsize button down shirts to get them to button without gapping but then the arms and shoulders are too big. My go to pieces on top are matching cardigans & tees or tanks in a variety of colors (brights & neutrals) and different necklines and sleeve lengths. On the bottom, look for a-line skirts in non-clingy materials that will flow off of your widest part. Same for pants as a boot cut or wide trouser leg will balance out hips better than a tapered leg. Always buy pants that fit your hips and then you can tailor the parts that don’t fit. I like to go neutralon the bottom and bring in color more on top. My staples are a pair of solid color pants in black, gray, olive, tan, and dark brown, and a pair of black with a thin pinstripe and one in a gray herringbone weave pattern. On the cheaper end try express or loft or gap to start building up basics and then work up to nicer stores for a few great items to mix in. To snazz things up a bit, look for cute necklaces and bracelets. A little sparkle even if it’s a $10 necklace from target finishes things off. I suggest you stay away from fake metal jewelry and go with beads or stones when buying cheaper jewelry. Good luck!

  9. I went back over everyone’s comments, and I have tried to compile a list of things to look at. If anyone sees anything that I have left off or is a must or is listed but I should remove, please let me know. (Remember, I’m on the heavier side with a chest and bottom)

    Personal Shopper – Nordstrom, White House/Black Market, Brooks Brothers
    Tailored outfits
    Various Jewelry and Belts
    Shoes – Have Black, look at shades of brown, olive green, purple
    Possible Dresses
    Pencil or A-line skirts
    Tops – lighter colors; cute designs; different sleeve lengths
    Trousers – Boot cut or wide leg; (black, olive, tan, black/gray patterns)

    Also, I was wondering just how big everyones wardrobe is?

    • I think the size of everyone else’s wardrobe is not as important as something you feel is manageable. That said, I think having options that work in different settings is more important. A must is a full-on suit that can be broken up (no reason not to make it a pants suit). Since you did not mention that you have a suit, I assume that is not a daily requirement in the rest of my suggestions. Round off your top with a few tailored/structured cardigans and maybe another blazer. For layering, get a few silk tees and button-up blouses in silk. Keep the pants you have and maybe add two more pair, maybe one in a pattern. If you want to add a dress or a skirt, feel free, but that is not mandatory, even in Dallas. For “flair” try some silk scarves tied as a cravat or knotted like a loose tie and even interesting belts if your pants have belt loops. That can add color and interest without forcing you into the realm of jewelry, which can be complicated if its not your thing.

      My personal opinion is that an executive, you should probably be able to go two weeks without completely repeating an “outfit.” That does not mean repeating pieces, just not the exact same combination. My executive goes about 6 weeks to two months without repeating (CFO for large non-profit). I’ve never tracked it, but she definitely rotates her clothing enough so its not noticeable that she is wearing the “Monday” blouse again. She has a very classic and simple style –using the pieces I have listed above. She has never worn a dress. She does have some skirt suits and a few more casual print skirts she matches with a shell and cardi. She wears the same diamond pendant every day, a watch, small earrings and maybe a bracelet. At Christmas, she has a few sterling silver pins she clips to her blazers.

  10. I feel more comfortable in pants than in dresses and skirts so I’d say a basic starting wardrobe would have at least 5 pairs of pants. That way you have a week’s worth of bottoms without repeats. Although if they are basic and neutral colors, you could easily repeat pairs if needed and nobody would notice. Black pants are black pants. As you find skirts you like, add 2-3 of those, especially if they are more comfortable in the summer heat. They are easily mixed in if everything you have is complimentary color-wise. To make them last, I take off my work pants when I get home, spot clean if needed and then hang them up for a second wearing. I only dry clean or wash after one wearing if really wrinkled or stained. For tops, you probably would want at least 10 top options since they aren’t as easily rework and they are more noticeable on repeat wearing. You’ll need mostly tops that can be worn alone or as a bottom layer and then you can mix in 2-3 top layer options like a blazer or cardigan. Again, make sure everything can be mixed color-wise. For shoes, you could get by with a black pair and a brown pair but I suggest getting one more pair in a fun texture or color for variety. I like having a pair of burgundy red flats or heels since I often wear all black or black and gray. Nobody will notice if you repeat your shoes often as long as you keep them in good shape and buy new ones when needed. I hope that helps!

  11. I would pay attention to how people talk about how you look. I tend to get a bit lax at work sometimes (I am always bouncing between courts and running around, so there is temptation to be comefortable), but I noticed that when I wear a dress or actually TRY and do my makeup or hair people in the office comment or ask if I have a date. This sparked me to wear more skirt suits or dresses. Dresses are the easiest, no thinking involved and you tend to look more sophisticated.

  12. UPDATE:

    I’m not sure if anyone keeps up with previous articles, but I thought I would post an update.

    I took your advice, went to Nordstrom and took advantage of their personal shopper. While I went in thinking I would spend $150 – $200 on a couple of pieces, in the end, I spent $800.00 on several pieces.

    Normally, this would be a bad bad thing, but it was just the opposite. I had a great time and I love my clothes!

    Normally, I hate shopping. I never find anything that looks good given my body structure and lack of color coordination and after a while I simply get tired, depressed and leave. With the personal shopper, everything was already picked out waiting for me in the dressing room. I found that I wear a 16 petite and I picked up some staples along with some cute clothes. ACTUALLY CUTE clothes!

    I don’t know if I can afford shopping at Nordstrom often, but I know if I shop there in the future, I will always use their personal shopper.

    As for the items, well, I purchased the following:

    a black ankle length skirt
    a couple of tops (purple, brown, turquoise)
    a blue and green scarf
    a brown cardigan
    a couple of sweaters tops (I get cold easily and winter is coming)
    a pair of dark brown pants
    a pair of nude shoes
    a set of earrings and a necklace

    While I believe I still need some more tops given I usually repeat clothing every week, I am very happy with my start and I appreciate everyone’s helpful advice.

Comments are closed.