The social system has always been able to successfully teach the young generation distinctive properties of each component of the environment and their functions. At an early age, children are taught both formally- in school- and informally- at home the differences and similarities between man and woman. No one ever confused both till this decade. In the past, it was a taboo to be caught behaving or wearing clothes of the other sex and some attracted penalties never thought of in our present age. We could put the blame on fast growing technology exposing young minds to unspeakable habits or industrialization eating deep into the time most parents are supposed to have to train their children on social values, ethics and responsibilities. Both have wrecked havoc in young minds in the name of modernization or civilization. Though no one can specifically pinpoint the origin of cross-dressing, it could be linked in a way to same sex relationships. In history, some women that wanted to gain employment but could not due to their gender decided to dress like men and secured employment to fend for themselves. Presently, in more developed countries, individuals could decide they fit better in the society as the opposite sex and change their gender through modern technologies. Many others in developed countries and some in less developed countries that cannot afford to pay for the surgery simply dress like the opposite sex till they are fully recognized as one. This is called cross-dressing. Cross-dressing as other habits never starts in a day but must have been developed over time or copied from social media by a young individual and never curtailed by parents or family. Every child do have the tendency to cross-dress for fun while trying to fit in but gradually sheds behavior such as he or she grows. Children may try this with sibling’s clothing, parent’s clothing’s or other related family members. There is always an exception to this rule though as some children never cross-dress while some never shed the behavior. Some cross-dressers have also been suspected to have mental disorders though it is not applicable to all. Socially, cross-dressing has thrown the world into a state of confusion where it cannot distinctively distinguish between both sexes by their dressing alone neither by their facial appearance. A man can decide to be putting on female’s clothes and make-up and vice versa. Infact, one has to verbally confirm the gender of an individual and not assume what one sees. A female might decide to identify as a male, dress as a male and demands to be addressed as one to the applause of a generation that is gradually loosing its social sense. The fame of cross-dressers on social media has increased the numbers of cross-dressers as some develop this habit of confusion just for fame and wealth. They are employed as social media influencers and brand ambassadors because of their growing fame. This social support is responsible for the rise of cross-dressers in the country. Rather than shun them, they are celebrated as social media now celebrates the abnormal. No country has laid down laws and penalties against cross-dressers as compared with same sex relationships. Cross-dressers are not seen as breaking any law and are not banned from such confusing acts. Traditional laws are gradually getting lenient in bid not to chase their youths away, condoning practices ancestors would have loudly frowned at. Though cross-dressers are not breaking social laws, they are causing mental imbalance as growing children cannot be taught to simply recognize a gender by outward appearance. Artists and comedians of this generation have further increased this incidence. The most celebrated social media comedians are those that cross-dress to act skit. There is a rise in male comedians dressing as females to act their skits and most are celebrated. This has further encouraged individuals to pick up cross-dressing as a behavior for fame. This has greatly influenced the society as society values and norms are beginning to have grey lines instead of the usual black and white. New definitions are created to accommodate this grey aspects of gender. This has resulted to social confusion which would further affect the coming generation. Cross-dressing is gradually becoming an accepted norm in various countries. If not curtailed, it would get to a point where no one would truly know another’s gender, crimes can be committed as a particular gender and the perpetrator would simply cross-dress to erase his or her crime prints. It is still early to draw the line to prevent further confusion. Osanyinro Oluwaseun, a graduate of Microbiology and currently a master student of Public Health at the University of Ibadan runs a blog on WordPress deejemima.wordpress.com