Say it Loud: Lipstick Tomboy, and Proud

by Sky Obercam

It takes a lot of effort to be a “girly girl”. A never-ending quest for physical perfection: Ones’ hair, nails, make up and attire must be impeccable at all times. Furthermore, who can overlook the tireless dedication to keep up with fashion trends, and the willingness to devote massive time and finances to maintain a flawless appearance? Many of these ladies take pride and pleasure in such pursuits, but what about the women who miserably strive to adhere to such standards – and the ones who basically ignore them?

There exists a category of women who function outside the boundaries of traditional femininity. Bohemian Chic, Lipstick Tomboy – call them what you will – but they fall somewhere in between the ‘classic tomboy’ and the ‘ultimate girly girl.’ Lipstick Tomboys aren’t clueless as to how to be ladylike. Undeniably feminine, they are free of some of the restrictions dictated by the stereotype of femininity. She’s the chick who won’t flinch upon chipping a nail while making repairs to the toilet, and still rock the ish outta her sexy black dress and fierce low-heeled shoes when attending an event of a swanky nature.

Not to be misinterpreted as a dig at our prim and proper, pastel wearing sisters; however, it is high time the Lipstick Tomboy received proper recognition. These brave ladies endure a good deal of criticism, condescension (and false assumptions as to their sexual preference) by resisting standards that call for her to inconvenience herself for the sake of what others.

So this one’s for you. All the ladies out there who either constantly struggle to conform to ‘girliness’ or those of you who simply say “f**k dat!” – holla if:

  • You can’t remember the last time you bought shoes.
  • Don’t see the issue with rocking the same pants twice in one week.
  • If while on your yearly shopping spree, you are constantly on the look out for clothing made from material that rarely requires ironing.
  • You do not use (or own) an iron.
  • You’ve often been accused of being “laid back, ” or not being concerned enough about your appearance.
  • You care more about the health of your hair than the style of it.
  • Occasionally, folks have pointed out a hole in your attire and you act surprised (even though you know exactly how that hole was created, and how long it’s been there).
  • You could care less what your eyebrows look like.
  • If you think confidence is sexy, not clothes, shoes or accessories that make you feel stiff and/or feeble.
  • Tend to despise pastels and floral prints.
  • You haven’t worn a slip, or even seen one since you were 6 years old.
  • You can’t recall the last time you read a fashion magazine.
  • When you go out on the town with your girlfriends, they resent that you get more attention from the fellas even though they spent twice as long gettin’ all gussied up for the manhunt.
  • Will not think twice about jumping into a pool, taking a hike in the woods, or any spontaneous act of fun that requires dexterity and exposing yourself to li’l grit ‘n’ grime.
  • Never had a mani or pedi (or are not quite sure what exactly they entail).
  • Don’t have a meltdown if your hair gets wet, or get a spot on your clothes.
  • The older women in your life look that seem to look at you with a hint of pity are the same folks that buy you manicure kits, frilly scarves or, pink homely sweaters on your birthday.
  • Are completely baffled by the form and function of church hats.
  • Have an aversion to purses and multiple accessories.
  • You think formal apparel resembles some kind of fancy straightjacket.
  • While shopping, you are guided by what looks right for you, and what works for your wallet – you could give a crap about a name brand.
  • Rarely ever wear make up.
  • You are more concerned with what makes you feel good, than what others say make you look good.
  • May as well pin a sign “I hate stockings” on your dresser.
  • To you, style and comfort go hand in hand, end of story.

There is a huge difference between low maintenance and no maintenance. True femininity doesn’t come from what’s on the exterior, but the qualities we possess inside like gentleness, warmth, sensitivity. Lipstick Tomboys are clean, stylish and confident living by their own definition of womanliness. It’s not about “I don’t give a freak about how I look,” but “I don’t give a freak what others think about how I look.” Let that Lipstick Tomboy flag fly high. Despite what “they” say, you’ve got a lot to be proud of.

  • monique

    In a nutshell this described me to a “T”. Great article ;)

  • Dreaming

    I’m definitely a low maintenance woman. I consider my look to mostly be androgynous.

    Some of the items on the list apply to me, but what I most agree with is, “To you, style and comfort go hand in hand, end of story.”

  • Krysie

    Definitely me all the way!

  • Candy 1

    Some people like me fall in between these feminine labels. I went shopping for spring/summer, and almost everything except a pair of jeans were dresses and skirts. Some days I care how I look down to the last baby hair and must look impeccable in every way, and others, I feel fine in a frizzy, messy ponytail and a plain tee w/ slightly too-big jeans. Either way, I always feel like a woman.

  • Crystal

    One time for the Lipstick Tomboys of the world!!! I fit just about all of those points made.

  • African Mami

    You could care less what your eyebrows look like.

    oi. stop. eyebrows need to be done!!! they are soooooooo sexy!

  • starr

    I like this article, because I fit it. I do care about my eyebrows, and I own an iron, but ony iron when I have to look put together, but pretty much me.

  • Leo the Yardie Chick

    I mentally ticked off a lot of things on that list. So me in so many ways.

  • Pseudonym

    hahaha! I thought the same thing. I may not wear makeup and have on some relaxed clothes, but the eyebrows will still be done.

    They instantly make you look put together, even without makeup.

  • binks

    Agreed! I draw the line on a few stuff on the list but for the most part the list describes me.

  • Velma

    I love this article… makes me smile. While there have been times in my life that I loved wearing that Brooks Bros blouse, a-line lined skirt with a pair of leather high heeled sling backs; I have since looked back on that in laughter. I no longer buy new fashions or the latest make up trend and love my natural hair. I love being comfortable and confident. I get a good laugh when I encounter the women in my family (aunts or cousins-who I really don’t interact with anyway) and they look at me like I’m such a lost soul—I laugh my ass off. I’m me and that’s all that matters.

  • t..

    repost? i’ve seen this here before. i still love it though lol

  • LemonNLime

    I would say 90% of this is me. I never thought of it as lipstick tomboy but maybe that explains people always tell me I’m just Bohemian/global chic. I’m always like what does that mean?! Because I like cotton dresses and sandals and bronze jewelry and like running around in the rain?!

  • Hushpuppies

    Yes yes and YES–this describes me! Some of my male friends and former love interests are shocked at the fact that I like getting facials because I ‘don’t seem like that kind of woman’ (how reductive), and have often asked me why I don’t wear heels and dresses, (on a non-fancy occasion, the horror). Because I need to be comfortable! I’m an active lady– and besides that am an URBAN girl. I need tennis shoes because if something goes down, I need to be able to run. I also ride my bike; how would I be able to do that in stilettos? And fake nails won’t do, they would get in the way when I play bass.

  • Chrissy

    i always had a thing for the tomboy feminine ladies!

  • Mimi

    Me? I wasn’t a Tomboy as a child. And i don’t consider myself as a lipstick tomboy either. But i do have plenty of friends who are still tomboys. Growing up, my tomboy friend were constantly teased and taunted for their tomboyish manners and ways. Accusations of being gay and “acting like a boy” were thrown at them on a daily basis. Even a few of my other friends would teased them by telling them that they were ugly and un-dateable. All of my Tomboy friends were the first ones to get married (one of my friends ended up marrying her childhood bully!) and have babies while the “high maintenance-girly girls” friends are whining about being single and childless.

  • MzDan

    haha!!! I totally agree with LemonNLime. Didn’t know if I fit Lipstick tomboy until I read this article. Always been told I’m boho. but I don’t fully accept that label as well. I do identify with at least 50% of this list. Love comfort (but MUST still be stylish), stopped plucking the eyebrows a long time ago, learnt a more efficient method that works for me.HATE, I repeat hate carrying purses! lol! cross body bags are my best friend (hands free people). Only buy shoes out of necessity. I almost hyperventilate when I seem to have more shoes/ clothes than I feel I need. Mani or Pedi is an option not a requirement. Phew! my list goes on and on. yay! for us. lol!!

  • Steppa


  • AllisonMG

    About half of the points fit me, and half of them definitely don’t. I don’t think I could put myself into a style category. I’m more of a “theme of the day” type girl. One day I might look girly-glam, one day I might look bohemian, the next day I might look like Lara Croft from Tomb Raider. lol

  • sonali

    Amen to this article and to having your eyebrows done; the only worth while thing to fret about! lol!

  • omfg

    i thought i was the only one.

  • Dreaming

    I, too have experienced people being shocked when they find out I do ‘womanly’ things and have been questioned on why I don’t wear heels (I do wear them, just not often) or dresses. I also prefer to carry a messenger bag, rather than a purse, because I hate to carry things in my hand. I mostly wear flat shoes or tennis shoes, because I use public transportation and mostly walk wherever I go and doing that in improper shoes is not cool. I don’t do fake nails either. I prefer my natural nails, which I rarely ever polish.

  • omfg

    @hushpuppies – i ride my bike in skirts, dresses and occasionally in heels. lol.

  • Hushpuppies

    @Dreaming- Yeah I catch public transit and walk too, which is why I also wear a shoulder bag– it seems safer and more convenient than a tiny purse.

    @omfg- I’m impressed!

  • MrTruthTeller

    AMEN !!!

    •Don’t have a meltdown if your hair gets wet, or get a spot on your clothes.

  • Nikkisunshine

    This article makes me happy.

  • BFDuster

    All of this is me–but I have to admit, I LOVE PASTELS AND FLORAL PRINTS AND FLOWERS. *ducks to avoid any incoming projectiles*

  • Tra

    HAHAHAHAHA!!! Finally another name for me besides the Boho Chic!! I do have to admit – almost all of the things on that list is calling my name. However, I love some shoes – but since I haven’t had the time (or energy) I’ll be rocking my boots until I make the time to find those spring/summer shoes!!! P.S. doesn’t clear polish count as a manicure??? LOL!!!

  • Leonie UK

    Yep that iron thing is so me, but my eyebrows are on a weekly threading appointment. Funny that as I get older I see me being that purple lady wearing red and getting comfortable in that scene.

  • Sandy

    Now I know what to call I always said im not exactly a tom boy but im not extremely girly either. I don’t iron my clothes ever, only wear mascara and lipgloss and thats if i feel like it, i live in jeans and besides a pair of earrings i couldn’t accesorize to save my life. On the flip side I do have to have my eyebrows waxed and I love shoes preferably cute flats or chuck taylors.

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