I have always tried to figure out how society determines what style of clothing each gender should wear, and how it came to that conclusion.
I am speaking as someone who is a creative person in the apparel industry. The reality is that most clothing designers have the wearer in mind when designing clothes, and therefore ultimately the designer is trying to play up the particular physical features of the wearer for ultimate flattery. Naturally, women have far shapely-er legs than men , therefore there fashion has always played upon the exposure of women's legs, whether it be short skirts, nylon stockings, etc. Dresses and skirts generally are meant to accentuate women's hips by flaring out in A-line fashion. High heel shoes create the feminine sensation of women prancing around like "en-pointe" ballet dancers. Plunging necklines show cleavage...a feature men don't have. The public's imagination increases with things like garter belts, corsets, stelleto heels, short dresses & skirts, tight clothing...all meant to show off feminine features that men do not have. Women may have better asthetics when dressing but the women's fashion industry exists purely to capture the imagination of the male mind. Otherwise we would all look like Chinese Mao-era communist subjects.
But in general, I have always though that men wearing women's clothing was nothing more than a square peg in a round hole. We men, for the most part, do not have the physical characteristics of females, therefore the clothing does not look the same on men as it does on women. there are many cultures across the world where men do not wear pants. In some cases, there really isn't a difinitive difference in gender style.
However, today, even women's clothing is not that much different than men's...but, that said, you will notice women's T-shirts have shorter sleeves and fit tighter, women's pants are hemmed above tha ankle to show leg, and women's tops show more chest area.
Fortunately, fashion rules have loosened up. Men can have long hear and wear earrings, however, note the style between mens long har vs.women, or men's earrings. Maybe the Beatles or David Bowie or any given rockstar have something to do with it, I don't really know.
But gathering at what I see of may crossdressers, tansvestites, drag queens, there is a heavy emphasis on short skirts, high heels, long nails, and sheer linegerie...all stuff intended to show off the feminine features of women...something many/most of us guys just don't have.