Tomboy Boot Camp

Katherine Moennig

“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 MoennigKatherine 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

A potential outfit!

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.

A potential outfit!

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