Halloween is the perfect time to use your creativity and think outside the box. Dressing your boyfriend as a girl, although not unique, will certainly bring entertainment and laughter to your next Halloween costume party. Use a few of your own accessories and make-up, as well as a little help from your local thrift store. The hardest challenge may be convincing your boyfriend play along. However, dressed in his new girlie attire, he is sure to be a hit of the party.
Design the outfit. If your clothing will not fit your boyfriend, make a trip to your local thrift store and pick up a dress or skirt and top to fit your man. Find a bra that will fit him as well -- and be sure to stuff the cups with balloons, socks or cotton.
Find a pair of shoes that fit. This can be the biggest challenge, especially if your boyfriend has a large shoe size. Remember that men's shoe sizes do not translate equally into women's sizes. Have him try on several pair and pick the one that fits best. Go with high heels for a dramatic look or flats for a more practical choice. The shoes can also be purchased at a thrift or second-hand store. If you absolutely can't find women's shoes that will fit him, go with something unisex like thong sandals.
Accessorise the outfit. No girl's look is complete without accessories, so your boyfriend's costume should include lots of them. Add jewellery, whether purchased or borrowed. Costume jewellery works well, as do clip-on earrings. Include a scarf, belt or a purse to complete the look.
Purchase a wig from a party supply store or costume shop. These can also be found in beauty supply stores. They are available in many styles including long, short, curly and teased. Style the wig however you wish, adding hair accessories if needed. Hairspray may also be needed to keep the look long-lasting.
Apply make-up. Make sure your boyfriend is clean-shaven to enhance the effect. Be creative, and use vivid colours for a dramatic effect. Add some false eyelashes to accentuate his eyes.
Give attention to his nails. Since many men are not keen on having their nails done, purchase fake nails from a drugstore or beauty supply shop. Place these over his real nails according to the package directions. File and paint if necessary.