Cross dressing men are nothing new in society, although it is only recently that they have felt free enough to cross dress in public without risking arrest or attack. Transvestism can manifest in a number of ways and can be as subtle or bold as a man prefers.
Brief History of Cross Dressing
Cross dressing has a long and complex history. It existed in the theatre from the days of ancient Greece until the Restoration, as women were not allowed to perform so men had to play the women's roles. Some of these roles were played by boys while other men specialized in playing women throughout their career.
The tradition still holds in English Pantomime, where the character of the Dame is always played by a man in elaborate drag. Drag acts were also popular in music hall and vaudeville. The tradition is so entrenched in British comedy that it was very naturally used by the members of the Monty Python troupe in their sketch show, with the men often playing overweight, middle-aged busybodies.
Drag acts were less common in the US, although many comics, including Milton Berle and Garrett Morris, used the form for great comic effect.
There are also many historical incidences of men dressing as women in order to perform espionage or gain an escape. However, in so far as an average man choosing to wear women's clothes simply because he liked to, the instances are little reported. It is understood that in private clubs catering to homosexuals - which had to be kept secret to prevent arrest - there were often cross dressing men. But little survives in the way of documentation.
Cross dressing has been slow to gain acceptance. It was assumed that men who wore women's clothes were gay, but gradually it's been learned that this is just a small segment. In cities, one will often see a man in full drag or in a more subtle she-male outfit, and very few people even blink. Whereas previously a cross dressing man had to sew and work the underground to find shoes and other accessories needed to create his desired look, there are now shops and web sites geared solely for transvestites, providing everything from foundation garments to false eyelashes.
Many transvestites will mix and match. Some will wear women's clothes but not attempt to be female - eschewing wigs, foundation and even makeup. Many also choose to wear male clothes most of the time, saving their women's clothes for parties and outings. They will often joke about how "boy clothes" are so much more comfortable than the heels, stockings and dresses they wear to be girls - jokes that gain them a lot of grim sympathy from women.
Issues Surrounding Cross Dressing Men
Up until very recently, homosexuality itself was considered a psychiatric disorder. Transvestism was often lumped in with it, hence the assumption that all transvestites were also gay. The look has inspired a lot of unnecessary confusion and fear, which has led to many transvestites getting attacked. It is still assumed by many to be a disorder. This is especially true when a cross dresser happens to be straight. Increasingly, this is being recognized more as a fetish rather than a circumstance requiring a mental health professional. Female partners of straight male transvestites are the ones who are usually the most uncomfortable with the circumstances. In this instance, a couple might visit a counselor who can help them both get to a place of acceptance.
Cross Dressing In Popular Culture
Cross dressing is still not widely seen on television unless it is a British comedy show, but the famous transvestite Ru Paul headlined a very popular show called "Drag Race" wherein men competed to become the next great drag queen. The show was very funny, but it also showed how arduous a task cross dressing can be, and how much commitment it requires. People may laugh, but they also had to admit respect.