There can be plenty of reasons for wanting to know how to look like a boy. From teasing your man, cross-dressing for a party, or making your decision about gender transitioning, these simple but effective tips would help you to trick the nature and turn into a handsome lad who knows how to charm everyone with genuine behavior and ease of manners. Read on to find out how clothes and some slight changes in your socializing habits can work their magic on you.

How to Dress Like a Boy

In this part, we will show you how to look like a boy by choosing a proper hairdo, make-up and, finally, clothes.

What’s about hair?

If you are serious about turning into a man (at least visually), you may have already cut your hair short. In this case, you don’t have to change anything about them apart from choosing your preferable styling. If you happen to wear long hair in the most womanly fashion, no worries – there’s no need to cut them. Just fix it with a styling wax and tie it up. Depending on your chosen look, you can add a cap or a vintage hat to cover your long hair.


What’s about make-up?

Despite the common opinion that boys don’t wear make-up, some of it won’t hurt. Think about the pop culture ‘divas’ like Boy George, Brian Molko or Adam Ant – you can even cosplay them in some peculiar way (especially, if you are doing this for a fancy-dress party). The secret is to find something suitable for the occasion – from glitter eyeshades and funky moustaches drawn with a black pencil to plain foundation and just a touch of mascara, there’s much room for experiments.

If you go for a cosmetics-free option, make sure your skin is well-moisturized and looks soft and fresh, because turning into an opposite gender doesn't mean abandoning your best skincare practices.


What's about cross-dressing?

Depending on where you are going, be it a casual city stroll or a formal event, you can choose from a whole array of options.

  • Start with unisex

    In your quest for an ideal male look, you may find yourself insecure and hesitant about taking it all up upfront. To lessen a possible discomfort from switching your clothes, shop for some unisex clothes first. Here, some cultural inspirations may be helpful. For example, in my first attempt to cross-dress, I went for a white-shirt-black-pants version of French students' wardrobe of the 1968 Revolution era.

  • Choosing a role model

    If it's difficult for you to come up with your own look at the very start, try some sort of creative borrowing. Choose a role model from the male pop culture figures - straight or homosexual, and steal their defining attributes like their silhouette, top-and-down combo, choice of brands and color schemes.

  • Everyday casual

    If you are curious about how to look like a boy in your everyday life, not special occasion, just forget about dresses and tight sassy clothes. Go for boyfriend jeans, baggy t-shirts of your favorite rock bands, loose white, black, grey or checkered shirts and a pair of sneakers or good old Doc Martins. For smart casual, there's no better inspiration than Ellen DeGeneres, in my opinion.

  • Formal suit

    Oh, this is pure gold. Having a dapper men's suit tailored to your waist and slopping shoulders is sexy and reminiscent of the golden days of cabarets and moral liberation, above all things. Turn to red carpet looks like those of Eddie Redmayne for inspiration.

How to Act Like a Boy

Now this would require a bit of preparation and self-control. It's tough to abandon your girly habits, especially when you have been practicing them for decades. But if you want to know how to look like a boy, imitating their posture and behavior is key to nailing the whole cross-gender experience.

Mind your body language

This is what will give you away at once. To keep it rolling, relax and lean back when sitting, with your legs slightly apart or, if you cross them, put the ankle of your right leg close to the knee of your left one. This is a typical boy's position that will add up more confidence and a sort of the 'so-what' attitude.

When walking, make your pace moderate and your steps wide, without rocking your thighs as this is a sure betrayer of your feminine nature. Don't cross your arms, and when smoking, hold your cigarette down, not up in front of your face.


Play their rules

If you are serious about adopting everything about masculinity, it's important to learn their social rules like proper greetings, conversational topics and the entire behavior that is considered acceptable among male friends.

Probably, you have a brother who could introduce you to this intricate etiquette. Or, alternatively, you can look through some more detailed tutorials online and look for some tips in movies and books. The only thing to keep in mind is that it really shows when a girl puts too much effort in playing a boy. If your intention is far from comic, try to behave as natural as possible, avoiding looking like a quite miserable imposter.


Tune your voice

This step is not necessary if you cross-dress for fun, though it could add up a comical effect to your whole performance. However, if you are serious about adopting as much as possible to look like a boy, there are a few ways to do so by paying extra attention to your pitch, pace and pronunciation. Again, looking for real-life examples really helps. Look up professional training materials on the Internet or consult people who have already done anything of this kind, whether they are actresses who know the tricks of the trade, or transgender men with a first-hand experience of tuning the voice right.


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