Costumes for men with a feminine twist will almost always elicit a reaction from others, if not outright laughs. The bigger or more masculine the man, the bigger the laugh he will receive if he dresses as a woman for Halloween. Although you can choose to invest a lot of money in a ready-made feminine costume, it is just as easy to create a womanly costume from items you can find around your house or from a thrift shop.
Sexy woman's costume
A man dressing as a sexy woman will almost always win many smiles, especially if he is a bigger man. One famous and hilarious example of such a costume is when Today Show host Matt Lauer dressed as singer Jennifer Lopez in an extremely low-cut dress. The dress was a copy of the scandalous, barely-there outfit J-Lo wore to the 2000 Grammy Awards. A man copying Marilyn Monroe's sexy look will always draw attention, and the look is not that hard to pull off. Find a large white dress, preferably halter style, a short blond wig, heels and lipstick. Hairy legs and arms and other imperfections will only add to the humour of the costume.
Famous "transvestites" or "cross-dressers"
Copying a famous cross-dresser is another costume idea for a man who wants to look like a woman for Halloween. Some of these costumes will be easier to create than others. For instance, to dress as the infamous transvestite Dr. Frank-N-Furter of Rocky Horror Fame, you must have a bustier or a black vest, gloves and garter belts, among other items. On the other hand, dressing as one of the Redskin Hogettes -- fans of the Washington Redskins football team who are known for dressing as women with pig snouts -- requires little more than an ugly dress, sunglasses and a pig nose.
Role reversal is a good way to take ordinary costumes and make them stand out from the crowd at Halloween. Instead of being a boring flapper girl as a part of a gangster couple, have the man wear the short dress, heels and a wig and then have the woman wear the flashy suit and fake gun. You can do the same switch with a wedding look by having the man dress as the bride in a white gown and veil while the woman puts on the suit and plays the groom.
Traditional women's looks
By far, one of the easiest and cheapest costumes for a man is a simple dress that he can borrow from a female family member or friend or purchase at a local thrift shop. He really doesn't have to add much more if he doesn't want to. However, most men like to embellish their costumes a bit. A pillow placed under the dress and held up with a belt can help a man look like a pregnant woman, or he can wear glasses, throw on a grey-haired wig and carry a cane to become a little old lady.