How to Dress and Act Like a Boy

So you're a girl, and you want to look like a boy. Maybe your transitioning, maybe you're doing it for a dare, a costume, or just because you want to change your wardrobe. This article will show you how to make people believe you're a boy.


  1. Image titled Dress and Act Like a Boy Step 1
    Fix your hair. If you have short hair, you don't really need to do much. If your hair is longer, you may want to consider tying it up in a bun or ponytail. Ask someone for help with this part, and buy a packet of bobby pins to keep flyaway strands in place. Once your long hair is contained, cover it with a snapback/baseball cap or a boyish beanie. You can get a cheap hat in the boys' or mens' section at your nearby Target or Walmart store.
  2. Image titled Dress and Act Like a Boy Step 2
    Get some suitable underwear. Depending on your breast size, you might need to buy a sports bra or durable binder to create the illusion of a flat chest. Stay away from padded/push-up bras, or ones with underwire. Invest in a sports bra - it will compress your chest nicely. If you want, you can also find some men's boxer shorts in the men's section of your nearby clothing store.
  3. Image titled Dress and Act Like a Boy Step 3
    Avoid girly habits you may be used to, for example... Don't cross your legs when you sit down, instead, lean back with your legs spread slightly apart. If you have a naturally low voice, you're pretty lucky! But if you're like most girls, you go up into a higher register when you get excited, which makes you sound feminine. Don't force yourself - you'll sound fake. Just talk in a lower, more monotone voice.
  4. Image titled Dress and Act Like a Boy Step 4
    Don't go overboard with makeup. You might think you know a way to look more masculine with makeup, but it's easy to tell that you're wearing foundation or contouring powder. It's best to wear none, even if you're tempted. If you really still look girly without makeup, try using brown eyeliner to lightly shade in your eyebrows.
  5. Image titled Dress and Act Like a Boy Step 5
    Find some boyish clothes that are comfortable, but not gaudy. If you're flat-chested you can pull off tight shirts, but otherwise stick with roomy graphic t-shirts, sweaters, or polos. Get some plain jeans or slacks in the men's department and make sure they're comfy. For your feet, stick with plain white or grey-colored socks and basic sneakers/Converse.
  6. Image titled Dress and Act Like a Boy Step 6
    Remember - act natural! Don't force yourself to act out some idea of what "masculine" should be like. Just cut loose and have fun!


  • Make sure you remove all leftover makeup with cold cream or face wipes before you go out.
  • Add 21 to your lady's pants size to get an approximate waist size of the men's pants you will wear. (Example: Size 12 + 21 = 33" Waist)
  • To convert your women's shoe size to men's, subtract 1 1/2 sizes from your regular shoe size. (Example: Size 9 1/2 women's - 1 1/2 = Size 8 men's)
  • Ask a male friend you trust for help deciding what to wear or how to act.
  • When picking out a shirt, choose something a size or two bigger than what you'd wear in women's. You can be liberal with this.
  • Make sure you try everything on before you buy!
  • Hang around your guy friends - it's more believable than being the only boy in a group of girls.


  • Don't try to use Ace bandage as a chest binder - it can cause breathing difficulties and it's just not reliable!!
  • If you want to purchase a chest binder, invest in a quality one from an online retailer.

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Categories: Fashion Styles