It is curious that cross gender expression is socially more acceptable for particular sexes at certain age periods in their lives. What is even more curious is that this social acceptance, at least in western society, is almost diametrically opposite for men and women although this changes with age. Let me explain.
From birth until the onset of early non family socialisation (typically 3-4 years) certainly with the family unit it is quite acceptable for a broad range of gender expressions to be acceptable for either sex child. Toys for this age bracket are typically genderless, clothing is also fairly genderless at least in a casual setting and even more "formal" clothes are often of similar form and differentiate the genders by colour.
In the next stage of peer socialisation (from ages 4 through to puberty) there is considerably more restriction of gender expression for boys with a strong expectation of typical "boy" play with cars, trucks, toy weapons etc. Boys who play with dolls or cooking sets or dress ups role play even when the dress up is a "male" dress up are often strongly socially criticised, the term "sissy" often used and they are often actively discouraged or prohibited from any sort of cross gender expression. The wearing of anything other than pants and a shirt in any social setting is highly frowned upon and discouraged or prohibited. Curiously girls in this age bracket have far more leeway in terms of their gender expression. "Tomboy" is a label that carries with it an element of pride "She's our real Tomboy" is often heard. Girls who play with cars and trucks are seen as being assertive and praised. Girls in this age bracket have a wide range of clothing choices in almost all social contexts and will be accepted in almost all social environments be they wearing pants and shirt or skirt or dress.
The onset of puberty however sees a marked and dramatic shift in the ability of girls in particular to express their gender. The 16 year old "tomboy" is no longer praised for their assertiveness and pride is replaced by a wishfulness on behalf of family and society for the individual to strictly conform to social expectations of their birth sex. "She could be so pretty if she just wore a dress" is a phrase often heard to describe the tomboy teenage girl. Worse still the sexually mature girl who does not conform to social expectations of her gender and she now is the subject of rumour and innuendo "Maybe she doesn't like boys" or "she will never find a good husband if she doesn't start behaving like a lady". Any strong close female friendship is scrutinised and criticised. Conversely boys at the onset of puberty actually find they often have far more freedom in their expression of gender. Long hair in boys of this age is often praised as a sign of individuality and rebelliousness. Even makeup is not socially prohibited with boys who may chose to wear makeup being regarded as artistic or thespian rather than ridiculed as "sissy". Similarly with clothes boys start to have much more choice in terms of fabrics, colours, patterns, even to the point where whilst unusual a teenage or early twenty something boy in a skirt is socially tolerated and again often praised for their individuality. Close male friendships are regarded as quite normal in this age group and indeed encouraged with the individuals in question widely regarded as being "just really good mates".
We now move in to the age of family and career. From the age of 25 both men and women have extreme social pressures and expectations placed on them to conform to societal gender roles. Women are expected to rear the family and provide a stable home environment for their husband whilst a husband is expected to push and excel in his career with praise and reward being received when he places career ahead of family.The woman who wishes to pursue her career is regarded with suspicion, she is thought to have an axe to grind and another one of those "feminists". Her husband is regarded with similar suspicion particularly if he supports her in those endeavours and is regarded as "weak" or worse "cuckolded". Here we find men particularly are expected to fall back into socially acceptable gender expectations. It is no accident that the rate of uptake of parental leave among fathers is less than 10% in most western societies. The new father who wishes to take parental leave is often firstly flatly refused followed by a begrudging granting of their request with the caveat that "this will set your career back, possibly permanently" despite numerous legislative stipulations that this is not only immoral but illegal. The freedom of expression in hair length, makeup and clothing style is dramatically curtailed especially if the individual wishes to progress with their career, whatever that may be. Women do regain some of their previous freedoms of expression and they do have the opportunity to pursue a career and family life though with a thick skin as they field the thinly veiled criticism of "I don't know how she does it." implying that something somewhere is amiss. She regains the ability to wear a larger variety of clothes and less makeup as her husband gives her the legitimacy of clearly being heterosexual thus the innuendo of her maybe "not liking men that much" if she chooses to wear pants and a shirt is now dropped in favour of the somewhat hypocritical "well, she can't be expected to look pretty all the time with having a career and looking after the children and the house". So a woman has the paradox of whilst being able to regain some of the freedom of gender expression she previously had, it comes at the expense of praise of others and often her self esteem.
Finally we have the age of what I will call social retirement. This is sometimes accompanied by work retirement but not always. The individual has fulfilled their parental duties, children have left or are soon to leave hoe and become independent. They have reached the maximum height of their career advancement and can either go no further or have no wish to go further as they have finally achieved the financial and career goals that they previously had. In the absence of these social expectations and duties the individual once again finds themselves far freer to express themselves as they wish. Again a woman finds herself freed from social expectations to be uber feminine or the ideal housewife at dinner parties and has a wide variety of styles of dress from pants through to full length dresses to choose from all of which are acceptable in a variety of social settings. Short hair is also again widely accepted as being "easier to manage" and she is now free to pursue whatever interest she wishes and in most cases is encouraged to do so. Similarly men also gain the freedom to express themselves in far more flexible ways. It is now acceptable as a "grandfather" to eschew career opportunities in order to spend more time with family and grandchildren in particular. He regains some of the lost flexibility of puberty in clothing and other presentation choices and it is now quite socially acceptable for him to again grow his hair longer if he so wishes or even colour his hair. Clothing choices as well, whilst perhaps not quite as flexible as previously, increase and colourful shirts, unusual jackets, distinctive hats and the wearing of jewellery again become socially acceptable for him. Even dressing in skirts or dresses is seen as somewhat of just an unusual hobby socially and attitudes from family and friends are not unusually along the lines of "well if it makes him happy and he's not hurting anyone" especially when such expressions are kept for nominated occasions such as fancy dress parties or at home.
The purpose of the above is to open free and frank, but respectful, discussion. Arguably when analysed over an entire society and whole of life experience cross gender expression is not a male only phenomenon and in fact exists in both sexes likely to an equal incidence and degree. Additionally BOTH sexes experience significant social pressure to conform to expected gender normative expression throughout their lives. This is not fair, for either men or women. What we must do is ensure that we do not encourage and perpetuate these societal prejudices inadvertently through our own attitudes. Comments along the lines of "Why don't women wear dresses anymore" are both inappropriate and show a lack of understanding. Similarly "he looks ugly in a dress" or "he/she would be so much prettier if he didn't have a beard" are also unhelpful and border on being hypocritical. We've all said these things, men and women on this forum and elsewhere, including myself. If we are to move forward and eliminate society prejudices to our expression of gender then we must first carefully analyse, question and sometimes yes endeavour to change our own attitudes to reflect a more inclusive, understanding and tolerant way of believing and thinking.
Thankyou for reading
Kate