Tomboy Boot Camp
[ 12 December 2007 ]
“I was a tomboy as a child, then as a teenager I had an ubercasual, slightly androgynous style (jeans/tees/trainers). But now I’m rapidly approaching 20 and desperate to look and feel feminine and sophisticated. I tried to throw myself in at the deep end by buying a couple of pretty skirts, but I feel overdressed and awkward so I’ve never actually worn them outside my flat. How can I ease myself gradually into this girly stuff (without feeling like a drag queen)? And how can I look feminine and still be casual for uni?”
Consider androgyny
Dresses aren’t for everyone, & there is no point forcing yourself to dress in a way that doesn’t suit your personality or lifestyle. If you’re most comfortable dressing like a tomboy, consider upgrading to a more androgynous appearance. There is nothing wrong with looking androgynous — in fact, I think it’s an incredibly sexy style. The difference between being a tomboy & a hot androgynous girl-thing is the polish. Tomboys don’t brush their hair or they just throw it back into a ponytail; androgynous girls have great haircuts which they tousle to make it look like they just finished having sex. Tomboys don’t wear make-up; androgynous girls use a bit of foundation to even out their complexion & smudge some pencil around their eyes to make them look smoky & mysterious. Tomboys wear ill-fitting jeans & a baggy t-shirt; androgynous girls wear fitted black jeans or tailored black pants & a skinny-cut business shirt or interesting vintage tee. Do you see the difference? Androgyny requires effort, as dressing “femme” does — it’s just a variation.
Katherine Moennig is the epitome of androgynous chic.
Work with your own style
If jeans & a t-shirt are what you’re comfortable in, use that as a base to start from. You don’t have to wear floral tea dresses & knit blankets for everyone you meet! If you like to wear pants, then do that — just approach it differently. Make sure your pants fit you. Pick a cut that is flattering, that makes you look tall & slender. Check out your booty in the mirror — a good pair of pants are like a booster bra for your bum, rather than a minimising bandage. Instead of buying big, loose hoodies, buy a cardigan that reaches your hips, a vintage tuxedo jacket, or a v-neck cashmere sweater. Basically, think of your original style, but make it luxe. That means quality fabrics & flattering cuts.
Dabble with jewellery
You don’t have to start walking around like you own a diamond mine, but a little bit of jewellery is a really nice accent. Think of it as a personal signature. Of course, given that you probably won’t be wearing much of it, make sure that you buy something you absolutely love. Your skin tone will tend to dictate whether gold or silver suits you better. Gold is good for warm tones (people with olive skin, for example), while silver, white gold or platinum tends to look better on anyone who is pale. A fine chain with a couple of charms on it makes for a really nice signature necklace, just like a couple of plain bangles or a simple ring will. You don’t need to go for the gaudy stuff unless you really want to. (I can never resist, but then, that’s just my style.) I always think it’s worth spending the money on good jewellery. You get what you pay for, & if you buy something that is good quality, it will last you a really long time.
Buy one skirt
This step is optional, but if you do want to venture into more feminine pastures, buying one skirt is a good way to start. The reason for only buying one skirt is that it is really non-threatening. If you end up never wearing it, it’s only one item — not five, so there’s less guilt about seeing it in your closet. Plus, if you buy well, you’ll be able to coordinate it with lots of things in your wardrobe. I would suggest going for a pencil, maxi or pleated knee-length skirt in a neutral colour like black or grey. You can wear any of those with a fitted t-shirt, singlet, vest or business shirt (loosened at the collar with rolled-up sleeves, please!).
Upgrade your footwear
If you only wear sneakers & would like to continue in that grand tradition, that is totally cool — but just step it up a bit. Buy a pair of decked-out sequin Converse, or glitter customised Nikes. Check out Sneaker Freaker for the latest information on the sweetest kicks. Alternatively, if you prefer boots, just move higher up the boot food chain. I am a huge fan of Frye boots, though a great pair of cowboy boots are always cool & very versatile. Now, for the really daring — high heels! Start with a low-ish heel, & see how you go. There’s no point in buying a 6” heel & then breaking your ankle! You can also try a kitten heel to start, though I agree with Victoria Beckham when she says…
“I think a lot of women see them as the wearable compromise to high heels, but in fact they have none of the benefits of high heels yet also none of the casual ease of flats. High heels elongate your leg because they pull up your calf muscles; kitten heels make your muscles tense & swell up; high heels hoist you up; kitten heels make you slump. But most of all, they make your feet look bigger: they emphasise the feet by having them point downwards. There is nothing wrong with big feet but in this case they will look out of proportion to the rest of your body.”
Anyway, it’s your choice! Read How To Buy A Good Pair Of Shoes & How To Walk In High Heels before you set off on a shopping expedition!
Grooming is key
As I said above, the one thing that separates tomboys from everyone else is the grooming aspect. Grooming — to me, at least — means having a good haircut & looking after it, taking care of your skin, wearing a little bit of make-up & having neat nails. It also covers a gamut of little things, such as wearing clean clothes, fixing any holes or rips, not having your underwear show above your jeans, etc. Doing all these things might seem like a lot of effort, but really it’s just like any routine. You’ll get used to it & the benefits are enormous. I know that I always feel much more presentable (& therefore good about myself) when I have a great manicure & an immaculate haircut. It will be similar for you!
Get thee to a make-up counter
Go to a counter you like the look of (I recommend MAC & NARS), tell one of the assistants that you’re trying to bust out of your old tomboy habits, & ask them to help you. They will probably be delighted. Like Cher says in Clueless: “Ooh, project!” Get the assistant to make you up & observe what they’re doing. Ask lots of questions & don’t be afraid — most of these people are in make-up artistry because they love it & want to help other people. When it comes to purchasing, I recommend obtaining a bottle of foundation, some concealer, a tube of mascara & a black or brown eyeliner pencil. A separate brush for your foundation & concealer are a good idea too. Take your loot home & start experimenting!
Empty your pockets!
No, not just when you’re paying for your new purchases! Stop storing things in your pockets! It is unsightly & silly. Buy a bag that you like & start carrying things around in that, instead. When you buy it, look at the hardware (the metal clasps). Are they gold or silver? If you want to look put-together, the hardware on your bag should match the jewellery you wear. Just a little tip!
Outfit ideas
Cropped tuxedo jacket by Oli; Disney magic castle necklace; t-shirt by Imaginary Foundation; grey cigarette trousers by Topshop; CC Skye leather chain bracelet; Betseyville Glitterati roll satchel; gold python belt by V.B.H.; Kenzie ankle boots.
James Perse cashmere v-neck; wool & cashmere fringed scarf; Marc Jacobs padlock heart charm watch; Falke over-the-knee socks; RM Pandora shorts; chap ankle boots by Steve Madden.
Feminising your tomboy style is a gradual process. You’re not going to wake up one day & feel like it’s time to float away on a cloud of gossamer petticoats — it’s something you’ll (hopefully) continue to tweak as your style & life progresses. There’s no sense in forcing yourself to dress in a way that makes you feel ridiculous, so just make little changes & see how you go. You will make mistakes, but don’t let that scare you off. Just see it as a normal stumbling block on the way towards a more refined you!
Extra For Experts:
Clothes Shopping Tips
Fashion Help For Recovering Goths
Hand & Nail Care
How Wearing Make-Up Affects Your Career
Making Short Hair More Interesting
How To Choose A Flattering Haircut
The Essential Guide To Dressing For Your Shape
Love letters & feather headdresses,
Tags: advice,
aesthetic,
consumption,
how to,
inspiration,
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Ooooh, fabulous! I’ve been reading your site for months & haven’t commented ‘cause I’m a shy creature, but I just wanted to tell you that I think your site is so lovely & your advice is always practical & useful. Also because I’ve been wanting to try a more androgynous look & this might push me to actually go for it…
& those shoes are amazing!
I want those sequined Converse desperately!
Toby — Aw, yay! Thank you! You should definitely go for the androgynous look, it’s so hot when it’s done properly.
Jessie Mae — Mmmmm, I know! Me too! I saw some silver holographic ones in a shop window yesterday & almost fell over. I am not a Converse kind of girl but they are REALLY awesome.
Ooohh, I love the pictures you’ve chosen for this article. Katherine Moennig is so hot. Please tell me someone else here took guilty pleasure in “Young Americans.”
I am so glad you wrote this! Just today I was feeling bad about not wearing girly clothes and reading this has really made me feel OK about how I dress!
Nadia — I never saw ‘Young Americans’ but I think K.M. & Sarah Shahi (oh, & Mia Kirshner) are pretty much the only reason to watch The L Word. Though, I am only up to season three…
katie — Awww! No, dressing like a housewife certainly isn’t for everyone ;D It doesn’t matter what your style is like, as long as you feel good in it, really.
The outfit ideas you gave have kind of a ‘mod’, which I love. I like to pair vests and bright tees with straight leg jeans and sneakers. It’s a cute, somewhat polished look. Love this post. XD
lcmo — I own kitten heels, so, you know. I just rephrased my article, because it’s not that they’re uncomfortable, they’re just not very flattering. You might as well wear a flat shoe!
Gala how do you do it?? I mean everytime I want something or need something you come up with a great artile on it.
I’ve been trying to be more feminine for a while now but I don’t feel very confortable in skirts (I just started wearing leggings). I live in jeans and T-shirts.
You just gave me great ideas for my shopping spree tomorrow.
Kisses.
I wish I could have read this about 5 years ago Gala! Great advice – I was going to go to my work Christmas party tonight wearing a tshirt and pants, but now I think I’m going to go for something a little more girly and put in a little effort!
Now I want to go shopping as well!
oh god, androgynous girls are PHENOMINAL and always make my head turn. there’s a certain element of style and attitude that only they can pull off, and just really make you stop in your tracks.
i think maybe it’s easier to relate to them, as well. in a bar or whatever, it’s style and attitude more than looks or plunging necklines that will catch my attention, and these girls will either be fiery and full of attitude and therefore a challenge and damn entertaining… OR they’ll be totally cool and laid back and easy going, which is also always good.
you really nailed the differences between them and tomboys though. you’re right, it’s like the next step up the food chain.
PS i’m seriously in love/lust with the girl in the top photo!
I love that first photo – where’s it from? I like absolutely everything she’s wearing, but what really makes it work are the way her hair and makeup draw attention to her face. (Which is, of course, the most important part of anyone’s body.) Then the jacket, hat and bracelets give a very basic outfit just a tiny tweak-up.
This is easily one of my favorite articles you’ve ever written! It’s about time there’s something showing how to work androgyny with style.
Let me just say that as a skirt/dress-wearer (owning more than 20 skirts, 5 dresses, and three pairs of pants), not all skirts scream girly and feminine! My own look is more “bookish” than girly. I’m just not comfortable dressed in a “feminine” fashion.
Don’t force yourself into a skirt if they make you uncomfortable (there are other ways to look feminine), but if you really want to wear one definitely follow Gala’s advice.
Gala, I love the suggestions and they will totally suit my own style.
pulls out moleskine and writes down Gala’s fabulous tips
Audrey — Haha, you & every bi-curious girl in the world. Her name is Katherine Moennig, she’s an actress & she plays a promiscuous heart-breaker on lesbian drama series The L Word. She is amazing! Even more amazing are all the rumours about her sexuality — everyone thinks she’s a lesbian but she is really secretive about it. Of course, that just adds more fuel to everyone’s lusty fire. So cool.
Nadine — I just found it on Flickr when I was searching for pictures of Katherine Moennig! She’s the perfect example of hot androgyny.
your positive comments on androgynous style are making me want to cry with happiness. I feel like I’m finally being understood!
although, as a hot androgynous girl-thing, I don’t find either of the outfits you put together very appealing. something about them is still too glossy and put-together- but that’s only my point-of-view.
Johanna — That’s okay, you don’t have to wear them! Obviously every outfit I put together on this site has my slant on it, which isn’t going to work for everybody. I just wanted to give people some ideas of how to do androgyny in super-stylish way!
Those pink heels are to die for.
This is such a great post… I was kind of startled at seeing Katherine Moenig because I JUST TODAY bought the fourth season of The L Word and am currently watching it.
She’s the absolute epitome of androgyny, I agree completely. So, so completely. If I were a skinny, pale girl with her complexion – I’d ditch this “lipstick” regime and steal her wardrobe. ;)
xoxo!
Ah, thank you so much for this! I really struggle with my style because I REALLY love the androgynous look (and like the girl who wrote the email, I pretty much dress like a tomboy right now), but it’s hard for me to pull off because my body type is chubby/curvy and certainly not androgynous at all.
But I think pulling in some more exciting accessories and wearing more makeup than just the most basic mascara+concealer will help a lot with feeling more “dressed” while still being comfortable. :) This is why I love iCiNG!
mmmmm….androdgny is so hot. I think its even hotter because the girls who do pull it off look really confident.
I think that even your articles on well dress men can apply to this (I think I even asked if I could do the whole skirt underneath t-shirt thing, but it didn’t look very good on me since I am little but rather well endowned on top)
white shirts + black skinny jeans look incredible when done right.
while i’m no tomboy, i do love this entry. very interesting! also, i love love love your shoe choices. :D
I’m forever trying to remind myself that just because I drool over sexy, slinky, sharp men, it doesn’t mean I should emulate their look. But thanks to this article I might just indulge myself a little less guilt free! I love androgyny on men and women, I love it when we join in that grey area. Thanks again Gala, daily helping your nonpareils to be more truly ourselves. xxx
Love androgynous girls and boys! Its certainly something difficult for me to pull off. I’m just such an uber-femme. Actually the pics and outfits were helpful in guiding me toward a less femme look. Not that I mind being the uber-femme, but its nice to shake things up every now and then.
I’m a bit envious of people who actually can wear pants constantly. They feel so stiff and uncomfortable to me, which is why I wear so many dresses and skirts. Leggings are the closest I get to pants, outside of my 2 pairs of jeans.
tomboy’s and androgyny is hot. i spend my time trying to look like an indie boy, and putting eyeliner on my guy friends.
and those converse are amaaaazing!
The first photo is from an October 2005 shoot in Interview Magazine (no, I am not that obsessed with Kate Moennig, but this is such a great resource: http://www.thelword-fr.net/katherinemoennig/uk/index2.php).
Any suggestions for a short, messy ‘do that might look good on a round-faced girl? That’s one of the reasons I’ve been putting off changing my style — I really, /really/ want to, but I have quite a feminine, rounded face & have not had short hair since I was 3! Plus for some reason a lot of stylists here have a lot of trouble with Asian hair…
i sometimes do the androgynous bit, my favourite thing is a man’s business shirt with the sleeves rolled up, wrapped round and tucked into jeans. the blue/white stripe ones especially. i was wearing that yesterday and on the way to the bus stop this stupid 14 year old boy was all, ‘do you have a penis?’. i got him real good though, i replied ‘no, do you?’
very good points on the hair and makeup, too.
Oh, Katherine Moennig is perfection. She does a wonderful job in the L word.
Also, those Steve Madden shoes have been on my christmas list for months now! They’re so pretty 8)
This would have been so useful 2/3 years ago when I was in my androgynous phase. I was so dowdy.
Now I’m in more of a girly phase, so I’ll just have to store this advice away for the future. Hmm. Although, I am tempted…
The last outfit [final photo] is so so so cute!
Great post, Gala. I NEED those sequinned Converse. I’m not really down with shopping online – where can I get them in Melbourne?
Toby — If your face is round, a fringe pulled to one side or long bits by your ears will help lengthen it out a bit. But your best bet is to speak to a good hairdresser!
sarahbella — I saw them in the window of a shop in Centre Place! You know, in that arcade thingy before you enter the laneway… I am not explaining this well but I’m sure you know what I mean!
Eee! I am in LOVE with that second outfit you put together, those shoes are AMAZING. I followed the link to see how much they were but it says they’re out of stock :( I really love the androgynous chic look, it’s so edgy and fresh and there’s loads of room to play around with your own personal style!
Great article Gala
xx
Great article! And i totally adore Kate Moennig. She’s so gorgeous. I love her effortless, chic tomboy style and cool confidence! I’m saving this article for later! Thanks Gala! :)
I was kind of a tomboy in my teens (I was an otaku! Black was my signature xD), but now I’m more feminine; I started to wear skirts as soon as I lost 10 kilos, I felt so good! So for some years now I have been more feminine x)
The only think lacking is a new hair cut, for three years I’ve been using a medium-lenght, layered hair cut, but I want a short one now, maybe with purple hair stripes :P
Oooh, cool fran, that’s exactly what I did to my hair when I got it cut- went from long and dark brown to short and blonde with purple! Changing your look gives you so much confidence!
I absolutely agree with Victoria Beckahm’s opinion on kitten heels…Ooh! And on the subject of Androgynous women, I met Erin O’Connor yesterday at Clothes Show Live – she was lovely.
I love this article so much! I was a typical sporty tomboy until about 2 years ago. Then I realized my love Victorian and fairy tale type clothes and I have started wearing more skirts,heels,and nice fitting clothes now that I’m in college. Androgynous people are awesome-it just takes confidence to pull the look off, and thats sexy.
great picks! love them all….Katherine Moennig is great on the L world but until you said it was her I didn’t recognized her in the pictures….and when you were describing androgynous girls I was thinking…..that’s Shane!! hehe and I love her look.
Guh! The androgyny look is so not for me, ever (I look rediculous, if not slobbish), but it makes me feel all fuzzy inside when done well. So lovely!
Mm! How does one achieve sex hair? hehe. I’ve always really wanted to know and have tried, but never really got it down.
I’d love to dress androgynously and I somewhat do now, just not…polished. I wish you could come here and be my personal stylist. ;)
Thank you Gala!
Thank you, Gala, for this amazing article. I haven’t really had much luck finding good articles on how to dress up when you’re not typically comfortable with skirts and dresses and this really is a great reference for a geek girl like me. Thanks again, and more power!
i loooove kate moennig (L)
she is so pretty and her style in the l word and in real life is sooo pretty, maybe is because she is gorgeous
Gala, I ALWAYS love your articles. :)
and this one amused me because that’s what I’ve recently been morphing for the past two years form a sloppy tomboy to a more attentive androgyny-esque style and now I’m slowly morphing from that to femme, although I do still shy away from heels. I’ve gotten a lot of flack for dressing that way though, kinda comes with the whole small town setting but I never let that get me down >:D
Ooh, I second the question about how one achieves “sex hair.” I’ve definitely tried, but it’s difficult to achieve with short hair.
I love the androgynous style, but my current clothes are leaning more towards the unkempt tomboy. I’ll have to work more on that.
I too adore Kate’s style. Another person worth watching The L Word for is Tasha (Rose Rollins) in Season Four. She is gorgeous!
very cool tips. i just discovered katherine, and i dig her style
I was looking for a Tomboy look…Do you have any tips? The boy I sorta like…He’s like a Popular boy who hangs around Athlete, Tomboy, girls.
I feel lame…I looked at your ideas and they are great! but all those girls wear pants. And I can’t have 4 inches at least off my Knee. My knees are sorta bruised ALL the time…
I can’t have tatoos. It’s the dress code. I also have to have a shirt that doesn’t show my sholders.
dress code again. I know. Stupid dress code.
I know this maybe like TMI but I REALLY REALLY NEED you help!!! and I have (Sorta) long red-blonde-little brown-hair.
and lots of freckles…
He has sorta side-medium-dark-brown-hair.
Please help! (6th grader in need of Tomboy fashion tips! ASAP!!)
Just wanted to say:
This was the first of your articles I ever read (in January 2008, when I was still getting used to my short short hair), and I still go back and re-read it sometimes!
Through this you’ve given me
1. a secret crush on Katherine Moennig and
2. an excellent reminder that I don’t necessarily have to dress “frilly” to feel more fashionable and well-groomed.
Thank you so much for writing this particular article, and for continuing to write all the time! I enjoy reading. :D