How to Cross Dress to Look Masculine. For many women the idea of cross dressing to look masculine is exciting. For some it's just for the thrill of it but others truly feel they were born the wrong gender. Whatever the reason is, it's not too difficult to cross dress and look masculine. Follow these steps to learn how.
Take off the strappy bra. In order to look masculine you need to flatten your chest as much as possible before you dress. You can band it with ace bandages if your chest is particularly large or wear a constricting sports bra.
Place a Nerf ball in the masculine region securing it in place firmly with a jock strap. It flexes comfortably and really makes the whole cross dressing effect look more believable.
Sport some boxers under your pants. This will pull the pants away from the curve of your bottom making it look flatter.
Buy men's pants that fit correctly over the hips as you pull them up to dress. If they fit correctly around the waist then they will pull around the hips revealing your curves. Put on suspenders to hold up your pants, not a belt.
Grease back your hair if it's relatively short. If your hair is long, braid it tightly or pull it in a low tight ponytail. You may also stuff it down the back of your collar.
Wear a man's tank top with a button front shirt over the top. The looseness of your shirt will disguise your figure making you look more masculine.
Apply facial hair if you desire after you dress. High-end costume shops such as Kryolan carry realistic mustaches, beards and sideburns.