Privilege Blog

Do Women Over 50 Make Good Tomboys?

Katherine Hepburn carries firewood into her E. 49th St. home

There’s a song that always used to make me cry. I’ve mentioned it before, Dar Williams’ “When I Was A Boy.” Here’s a sampling of the lyrics.

And I remember that night
When I’m leaving a late night with some friends
And I hear somebody tell me it’s not safe,
someone should help me
I need to find a nice man to walk me home.

When I was a boy, I scared the pants off of my mom,
Climbed what I could climb upon
And I don’t know how I survived,
I guess I knew the tricks that all boys knew.

And you can walk me home, but I was a boy, too.

I was a kid that you would like, just a small boy on her bike
Riding topless, yeah, I never cared who saw.
My neighbor come outside to say, “Get your shirt,”
I said “No way, it’s the last time I’m not breaking any law.”

Reminded me of the freedom of girlhood, before boys find us.

Now let me say right here that I enjoy the company of men, and I adore my children, a direct result of having been, well, found. But let me also say, as I have before, that I struggled with male attentions. I would engage, often to be set aside, I would try to do my job, only to be pestered. I never got the hang of Queen for the Day, the young woman who glides over the throng bestowing favors like handkerchiefs.

Accordingly, when I read this article, another one on the invisibility of the over-50 woman, I was saddened.

“But why, with all their achievements and experience, were these women so lacking in self-belief?

Four in ten said missing out on male attention was a factor while for more than half, the presence of younger women at a social event was totally confidence sapping.” (italics mine)

Granted, the study was commissioned by a purveyor of menopause amelioration products, but still. It seems that in the best of all possible worlds, at this age we can free ourselves from the need for power in the male gaze, if we choose. We can ride our metaphorical bikes again, albeit most likely with our shirts on. We are no longer under the spell of the species calling to itself, “More, I want more!”

Which brings me, given the topic of this blog, to “Which shirts?” We fête women with Advanced Style, all varied and vivid wardrobes, right? But if one has always fondly remembered the days of scrambling through meadows, one might prefer to re-embrace dressing in commonly “masculine” garments. Right? To date, I think there’s no “Advanced Tomboy” site.

How about Lizzie Metzler’s Tomboy Style? Everyone featured appears to be 28, that is when they aren’t 19 in a vintage photo from Vassar. The only thing I found over-40 was a beautiful handbag. Ooops.

How about Tomboy Xchange? Focused on the 0ver-40, but way more tomboy than polished.

How about La Garçonne? Tomboy buffed to the point of brilliance. While their brand clearly focuses on late-20’s early 30’s creatives, they do showcase Joan Didion as a “Garçonne We Love.” That’s close. I don’t mind approximations. Who among us finds their precise style, hung on a web page all perfect like? All I ask is that my concept, and a few sound implementations, are supported. I will defend your right to ruffles and lace in turn, even if I have to lock myself to the bars on Bergdorf’s windows.

One final thought. As society loosens the concept of gender – driven primarily by those breaking boundaries of sexual identities – those of us driven by other questions of identity may benefit.


Confession. I’ve always been uncomfortable with the word, “feminine,” probably because I never was. Feminine meaning, soft, quiet, deferential; a wearer of soft fabrics and embellishments. But I never, ever chafed against being female. Perhaps we could discard the term, “feminine,” and expand “female” instead, giving everyone a place.

A place with good pants.

And what’s Katherine Hepburn doing up top, outside her NYC apartment c. 1970? Why, she’s our icon, in comfortable shoes. Maybe Julia can join us in a few years?

58 Responses

  1. It’s funny, because when I read the title to your post in my RSS feed, I immediately thought, “Of course – Katharine Hepburn certainly was!”

    And lo and behold…

    1. Yes, Ines all the way!

      As I turn 50 this year and so have been evolving my style over the past few years I see that things are changing for the over 50 woman in the U.S. I get a lot of inspiration from the over 50 icons in Europe, who seem not to care a whit about the attention men and I channel that with great joy. Yet those men are still appreciating us; my friends and I have noticed that when we travel in Europe and South America that men seem to notice and enjoy stylish women of all ages.

  2. Much I relate to, here, although I’ve never been what I think of as Tomboy. I have always resisted the notion of “femininity” and “masculinity” — so culturally determined and such a stranglehold on those who don’t fit the descriptions. I do love much of the aesthetic you point to — Katharine Hepburn has always been a style icon for me, although my body type means I have to be careful how/what I emulate. Ditto for Lauren Hutton, who I see as Glamourous Tomboy, no? (I’ll admit, I don’t really keep up with celebs and their style, but I’ve long admired what I’ve seen of hers). I didn’t know the song you’ve linked to, but I love these lyrics, and I’m often for a listen right now. Thank you for your Tomboy wonderfulness which so often gets me thinking early in the day . . . ;-)

  3. I don’t think we should discard the term feminine, some women very much embody that word, whilst others don’t, I think it’s that simple. I’ll never be a feminine woman, I live in sweats and trainers most of the time, I’m not into pretty fripperies, I don’t care for a dressing table with artfully arranged perfume bottles and unguents but many do.
    Female as catch all I find too perfunctory, we are large, we contain multitudes so I don’t think we should limit words/terms.

    1. @Tabitha, I just never liked that “feminine” seemed like the most iconic of “female.” As long as “tomboy” or “femme fatale” are on equal footing with “feminine” I’m all set.

  4. There is a lot here to digest and thankfully now have hopefully fixed my spam filter so that I again get your wonderful posts hot off the press. Before I read those links and think through I just wanted to say I’ve just listened to that wonderful song (twice) for the very first time and love it!

  5. I think Diane Keaton deserves to be included. I watched her on Late Night with Jimmy Fallon this week and she is a style icon for that Tomboy look….my husband said oh she looks like Annie Hall and I said Annie Hall is Diane Keaton….Woody just wrote the script it was all her.
    Katherine Hepburn is a classic….
    BTW I don’t mind being invisible at all!

  6. Oh what fun!

    I think of it as menswear style and of course there are women who wear it from childhood on. I love the style and the uniform. It doesn’t work for me, because like materfamilias upthread I don’t have the body type lending itself to the look. You do and it suits you fabulously. When I do “tomboy” style it will be the sort of menswear look worn by the Bloomsbury circle… a blouse or dress with menswear cuffs and collar. Maybe a man’s hat or boots or jacket – but always with some sort of feminine twist. I vote for keeping “feminine” though I don’t see it as synonymous with female at all. Just another style or look. Tomboy has been an androgynous look for a while. I think soon Feminine will be accepted as such, too.

    Aging out of the male gaze: big sign of relief here. Basically I feel like I’m beyond the random male gaze (catcalls and head turns) but still attract (enough) attention from more discerning sources, both male and female. I do not feel invisible yet. I feel much more powerful and comfortable not attracting attention on the street. That made me feel very vulnerable to forces outside my control. Okay, maybe there is a cloak of invisibility but if so, it is really rather magical in my opinion. I love it. It seems to me easier to see the world when you don’t have to worry about your place in it all the time.

    1. @anon, “It seems to me easier to see the world when you don’t have to worry about your place in it all the time.”

      Well there we have it.

  7. Along with others here I would say Katherine Hepburn, Lauren Hutton, Ines de la Fressange, all come to mind when you mention tomboy over 50, although I see Ines as something else, tomboy with a bit of feminine mixed in, if there is such a category. Tomboy doesn’t mean not female, doesn’t mean not attracted to or attractive to men. I think women can be allowed to be complicated.

    I grew up in a culture, Southern or just a subset I don’t know, where women were expected to be feminine but also entirely capable of doing whatever needed to be done, be it change a tire or handle a steer. But I never identified with feminine. I am not a girly girl, but I am also not a tomboy even though when I was a child I never combed my hair, could climb the highest trees, swing from ropes across rivers, and could play war with the boys, artfully throwing myself from the garage roof and over the neighbor’s chain link fence to roll, “dead” on the grass without injury as well as the best boy. But I also liked pretty dolls and wanted pink patent mary-janes. I still like dresses and heels and perfume, but I don’t like fluff and frills. At home I’m happiest in a man’s shirt and old faded ripped jeans.

    At almost 56, I feel more confident than at any other time in my life. I find those articles about women feeling invisible terribly sad, especially when they say they miss the attentions of men. And I don’t care if men notice me or not, at least not in that frivolous way that men flock around pretty women at parties. I’d probably be uncomfortable if they did, flock around me that is. That doesn’t mean I don’t notice men, it doesn’t mean I don’t like to be noticed, or don’t enjoy the company of men, I do. Truthfully, I don’t think I really cared in my 20s either. I was rarely the one that men flocked around, but I had my fair share of suitors. But maybe I was just lucky to learn early on that there are men who like smart independent women, and those that don’t weren’t worth the effort it took to pretend to be something I’m not. I’m sometimes think that mourning your loss of attractiveness and “visibility” actually makes you more invisible, while confidence and self assurance make you more visible and more attractive over all, at least to anyone worth their salt. It makes me sad that anyone puts so much weight on something so fleeting, something of which one really has no control.

    I love your tomboy style, and your sharp, thoughtful and thought-provoking posts, and the way you always make me consider something in a new light.

    1. @Mardel, I second all you say Mardel – couldn’t have put it better myself . Mum brought us up to be individuals , not just women who needed to be flattered & looked after . Fortunately I found a man who appreciates that .

  8. I use the name “formerlies” to describe this whole whack of 50+ women who have this sensation of loss, the loss of random male attention. There are a lot of women who never had it to begin with, they are the ones you ignored when you were in your so-called prime. I was a skinny nerd, studied IT in college in a class of 40 men and had zero dates. It’s a whole lot harder to be invisible at 20 than 50.

    The interesting thing is that when I turned 50 I put on some weight, grew an actual bustline and with zero sun damage, never having ever sunbathed, I looked 38 not 50. I had more male attention than I had ever received in my entire lifetime but the minute they find out what your “number” is you will be discounted, you’re not 38 oh you’re a nobody. Oh my God you can’t be THAT age, like it’s a terrible secret, you killed your mother as a child?

    That’s why there’s no point in doing the surgery thingie, a Christie Brinkley or a Jayne Seymour no matter how attractive, they have to just learn to let go, you’re always going to be a formerly.

  9. Agree about Ines and love the styling on that Julia Roberts shoot. I’m over 50 and a tomboy, so I think it works! I’d happily go to a place with good pants.

  10. I was never a tomboy, which implied some sort of athleticism (zero here), but rather some sort of arcane hybrid of shy and wallflower. Still, the man that I married was much Sought After, and still is. I remain mystified and blessed that he remains besotted. There are undoubtedly algorithms for the laws of attraction, and the sorting out of masculine and feminine, but perhaps they are best left to mystery.

    1. @Kathy, Well, I agree, I was never sporty, but liked to wander. Let us all praise the mystifiedly besotted;).

  11. Mardel, you got it right. The men I have enjoyed the most in my life were attracted to my independence, love of a good hamburger and live music. I was and still am a no-frills girl. I don’t feel invisible (although I’m not looking) because the ones who can only see youth are not interesting to me. The issue has always been the scarcity of men whose attentions I would like to have. :)

  12. As women we are fortunate to be able to express both our feminine and masculines sides openly. We are able to be fully human. Society is not quite as accepting of men expressing any femininity although attitudes are progressing perhaps. It would be a shame to give up the freedom we women have to be fully expressive…no matter if our leanings are to one extreme or the other or are androgenous. I personally feel more tomboy than girly girl and am over 50 as well, but I relish all aspects of my femininity and age will not induce me to change any of it.
    As to being “invisible”…I do relish that. Sorry to sound immodest, but I have always been attractive to men and I’ve never liked the attention, never liked being observed even though I’ve always been self-confident. Life is much more comfortable now that I don’t feel like everyone is staring.

  13. Well, being 61, I am aware of the fact that men no longer check me out. Frankly, I don’t care. It’s unfortunate that women lose confidence in themselves because men aren’t looking at them. In the full time RV community there are numerous examples of women who have said to hell with that, sold their houses, bought RVs and are now living a life they love on their own terms. All women should position themselves for that time in their lives. Never depend on a man for money or self worth.

  14. I haven’t read any comments, but I want to say this: I’ve never been a tomboy and I love dressing in a feminine way. We are all different. And, I think that is a good thing. Some of us love being a tomboy and dressing like one, and others of us always look for the feminine clothing. (And, some of us would not look attractive dressed as a tomboy.)

    I am not one who looks for male attention at age 62. But, by the same token, I am happily married–as are you Lisa. I think that may make a difference.

    And, who can say that a man of 50 or beyond is not yearning to be noticed by women.

    1. @Susan, Yes, I will defend the right of those to dress not-tomboy too. I confess to have been reacting to comments on my post where I wore shorts and a blazer. And to years of feeling chided for my discomfort with some “feminine” behaviors. But I would not presume to dictate a change for others, only an inclusion of more.

  15. I am fairly certain you don’t WANT to be Queen For A Day. The contestants with the most pitiful story won. It required much hand-wringing and handkerchief-twisting and sob-storying. (Also? many hyphens…) Sturdy Gals Need Not Apply.

  16. I was thinking the other day about “feminine” and “female”, and here you’ve spoken my exact feelings about those words. And you’ve acknowledged the influence of discussions about gender identity exactly as I would have!

    I do not feel that I’m “missing out on male attention”, by the way. I don’t think about where attention is coming from. I feel more empowered now (at 60) than I ever have before, and I have friends and valued acquaintances of many ages and some genders.

  17. Great post and comments. So much to reflect on. I have always been no frills and love my short hair. I am generally much more confident of my style now and what I like to wear. It does not mean that all my 20 year old anxieties have gone away just reduced in intensity and frequency. I was never aware of male attention but I think that is partly because I paid attention and sought out my choice of fun and partner.

  18. A very thoughtful topic. Given (historically) that men have also worn colour, ruffles and lace, I’m not so sure about the correlation of feminine with clothing. Or even with behaviour. I’m another who was mostly tomboy growing up, and with what my husband considers a disastrous tendency to quite competently do things for myself without giving him a chance to do it for me. I do find that curious…

  19. In general I find that the women in Sweden and Denmark dress very no-frills. So yes, the over 50 dress this way too.

    I recomend that you Google the Swedish designer Filippa K. In my opinion, it’s women like you that she has in mind when she designs. The designs are simple that they look nice on someone 16 or 70 if their body shape matches.

  20. I feel like standing up and cheering at this whole discussion. Tomboy expression for everyone who wants it, YES. I do feel that this fits into the “Advanced Style” aesthetic – what are the enchanting Man Repellers but the younger version of this?

  21. Well, if you were a tomboy (or a little princess) as a child, you will be one as you mature… Most women fall somewhere in between ultra-feminine and tomboy I think, and their personal style evolves with them. As for becoming “invisible”, I’ve always thought most women dress for themselves, or for other women. I admit that it means a lot more when a woman compliments my outfit than when my husband does (he would think I look cute in anything, right?) as another woman has no ulterior motif to say anything nice. BTW, check out Alice Carey in Advanced Style, she looks fantastic wearing pants and ‘masculine-feminine’ style…

  22. Such a fantastic post and comments, well, save for the spam – although I do find “pretty element of content” a rather interesting happenstance considering what the content really is. ;)

    When I think of “feminine” the first thing that pops to mind is…the grace of a hand gesture…or a walk…a way of communicating with others. I know how old-fashioned that might sound but is the idea(s) that work(s) for me. And as Erika mentioned, it has nothing to do with clothing. I have seen very feminine women dressed in “tomboy” wear, just as I have seen more “masculine” women in high heels and dresses…

  23. I’ve always hesitated to call myself a tomboy, as although I played sports and skied, I was never a star athlete, and I was just as happy reading as being on the field. My clothes tend toward the menswear (Ann Mashburn is my go-to source, and I’d offer her as a “tomboyish” style icon any day), but with a very slightly feminine twist. My hair is longer (not as long as Lisa’s, yet) mostly so I can put it up when it gets in my way. I like heels and wrap dresses but, like Katherine Hepburn said, heels make it hard to move fast, and I do a lot of walking between buildings at work in DC. I love reading everyone’s comments here – while my style is pretty established, hearing others’ interpretation of terms and their read on the “invisibility” issue is a topic that never ceases to intrigue me. I feel so saddened by women who feel this way, and as others have said, trying too hard is never a good thing.

  24. Katherine….sigh. Was just on that block in NYC. Or so I think. But as a married with 2 kids turning 50 in a year and a half or less — I am fine with not being in that spotlight – I think there is quite a bit of freedom – knowledge gained? – in this age. But I wonder if I was single how I would feel. I feel like I can be bolder – brighter colors, mixing patterns (because I love patterns – uniqlo moma collaboration!) – cowboy boots – because I am worried much less about fitting in or conforming. And skinny jeans. Still wearing them. When do I have to stop? I’m not sure.

  25. Someone once told me I didn’t have the personality to be invisible. Not sure if that’s a compliment. As a happily married mother and grandmother invisibility is fine. I still get lots of attention from my husband, so that’s a help.

    As to clothing style, I am a khakis and polo shirt kind of gal. No frills for mr.

  26. A place with good pants! Sounds like a good place to be.

    I’m quite feminine (although also direct to the point of brusqueness at times)but good pants are a universal good, I think. It’s a broad church, the church of good pants.

  27. Right in the feels, this post of yours!

    I too was a rampant tomboy, and I even remember on my third birthday, I suddenly felt strange running shirtless around guests. It made me so sad, because it was my favorite thing to do in the summer.

    I struggled with and still struggle with male attention. I have no idea how to handle situations like that gracefully or coyly. My ideal is a “You are attractive. Would you like to mutually attend a social gathering with other interesting people?” and a firm handshake.

    I love reading your blog because I have finally found another tomboy perspective, and because I feel like I may too look fantastic in that style in the future.

    Embracing being female took a long time. I think it finally clicked that ‘female’ didn’t mean I would be shoehorned into a role, wardrobe, or character traits that did not suit me. It was me being me, and by dint of me being a woman, I was womanly.

  28. Do we need a label: “Tomboy”, “feminine”, “sturdy girl”? At what age can we just say “I am who I am” and not need to fit into a category or a template? Feeling comfortable with ourselves, and who we have become, and making choices consistent with that: about clothing, lifestyle, whatever…can that not be done without a label to inform our choices?

    1. @Ellen, I find it helpful to label what was latent, in order to accept it. Then incorporate and move on. That’s what I did with the “High WASP” idea, now working on the Tomboy. I have no idea what will be next in identity narrative;).

  29. What about Tilda Swindon (53)? She is the most beautiful and androgynous fashion icon around. She’s even played men in films. Very tomboy and very cool.

    Patti Smith (67)? Who was actually mistaken for a boy by Alan Ginsburg. She’s incredibly beautiful and iconic.

    Both of which are still very visible and appealing to men as well. I don’t think that girly/tomboy is what makes a woman invisible to men. Maybe perception? I used to think I was invisible to men, but from what I understand, I was wrong about that. People like all types, we’re much more nuanced than the media would have us believe.

  30. I play that song by Dar Williams in my Feminist Theory class, just before we discuss Judith Butler.

    My notions on dressing have changed. In my 20s I piled on gorgeous Indian silver–earrings, rings, and cuffs, but prefer a considerably leaner aesthetic now: just my wedding and engagement rings on separate hands. And I’ve been wearing skinny pants with a lean blazer A LOT–always with outrageous shoes, because it’s fuss-free. Really, I can’t label this style with any kind of gender descriptor (like Mater, I resist the binary), but it feels like me, and therefore it is :-).

  31. I keep coming back to this post and deconstructing it in my own fashion. Tomboy, sturdy gal, good trousers. They overlap, but are not one and the same. Although I am in a traditionally male career and thrive on competing with male colleagues, tomboy never felt descriptive. Tomboy implies a physicality and love of sports – certainly not me! Sturdy gal – well, any single woman needs to master some practical skills, but again the sturdy preference for practicality and lack of “feminine” touches – not my style. Good trousers and comfortable shoes? Always. But best with a touch of feminine glamour!

    1. @DocP, I agree that these labels do not encompass everything, nor every one by any means;). And if nothing needs naming, even better really. I name because I grew up in a wordy family and a culture that doesn’t speak its name. Big gap to fill…

  32. Boyohboy – this topic is in the air a lot these days! And I get it – that it’s important for many men and women to disengage from the binary and be….whatever they darn well feel like. At first this was a bit of a puzzle to me though as I’ve always been androgynous and happier because of it! I got over boy problems and girl problems a lot faster than if I had seen myself as strictly ‘feminine’ I think. I’m 70 (!) and am super glad to be out of the sexual gaze of men or women. I wear my hair blazing red (a red not found in nature if I can find it) so I don’t have to worry about being ignored :)

    Blessed are the fluid for they shall glide and…flow.

    You’re so wonderful, Lisa! Thanks for every post.

  33. This post has sent all sorts of thoughts tumbling through my head and a situation at work today has left me unable to order them in order to pin them to the screen.

    In lieu of the thoughts that I hope will straighten themselves so that I may comment in a day or two, I’d like to say that your post and many of the comments resonate with me, while those comments that don’t speak directly to me still open other avenues to explore and point to questions to answer.

    I’ve never heard of that song before, but it really struck me deep inside. While I fit fairly neatly within the historical gender binary, it is sad that those who don’t or who move fluidly along the scale are othered by sections of society, and that the push to binary starts at such a young age. ANd all the other feelings that follow on from there…

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