Halloween gives children and adults alike permission to let loose and dress up. Some people go for run-of-the-mill costumes while others opt for outrageous outfits. A man can put himself in the shoes of the opposite sex and dress up as a woman for a fun and easy Halloween costume. A trip to a woman's clothing store can be intimidating, but he needs only a few key items in order to successfully dress as a woman.
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A man dressing as a woman might be most comfortable in either a skirt or a dress. He should choose a skirt with an elastic waist band so it forgives any excess belly fat. In pants, he should look for something with an elastic waist band, such as sweat pants or workout gear. Most men need a larger size to comfortably fit into women's pants, particularly jeans.
A wig completes the transformation from man to woman for Halloween. Stores that sell Halloween costumers typically also sell wigs, so a man should have no trouble finding tresses to impress. There may also be a specialty wig shop nearby that sells more natural looking wigs, though these typically cost more. A man can also purchase hair extensions, found in the make-up section of most department and drug stores.
Watching a man wobble around in high heels may be funny, but it's probably not a practical idea if he plans to walk around for an extended period of time. He should try a pair of women's flats, or go for heels no higher than 3 inches. For extra foot support, he can purchase sole support that can be slipped into a shoe at a drug store.
To complete the outfit, a man might want to put on some jewelry and carry a purse. A scarf or hat might also work, as well as make-up, including fake eyelashes and extra long nails. Typically, a man dressing as a woman for Halloween would want to appear as obvious as possible, so more garish make-up would be appropriate.