Underdressing

OK, gender-bending is not for you, you are not going out in public dressed as a woman and with your beard. And female masking is too expensive. What else can I do? For a lot of cross-dressers, it not all about looking like a woman but feeling like a woman. The pleasure is feeling something that has been reserved for the other sex that is exciting. Male clothing is called “drab,” And not all men want to feel like a woman, they want fashion freedom and choice to wear what they want and have options. Show off their fresh sense of style and what makes them who they are. Even woman get purses in beautiful forms, yes, we have wallets, but they only can do so much with them. Men's clothes are dark colors; the funny thing is we are nothing like the male peacock bird at least they know what brightly fun colors are. Men's clothes are basically, T-shirt, shorts jeans, pants suit, polo, kilt but not typical to wear, man-made fashion kilt style but again not common, long sleeve, button shirt, overalls but not common unless you do farm work, and yet all these haven't changed from being like each other just with either a different pattern or picture on it. Not changing the style, a shirt still being a shirt no matter what color or pic is on it vs. a suit still being a suit made of whatever material. (bomberman6 a 32 old male)

From Quora, Julia Reece, stated in reply to why do men wear woman’s clothes?

Men wear women’s clothing for many reasons, and here are some of the most common ones:

#1 - Many men adore women and want to feel as close to them as possible. This is one of the most common reasons why men wear women’s clothing - dressing in the same clothing that women wear gives many men the feeling that they are literally inside a woman’s body.

#2 - Most men have been deprived of wearing pretty colors and feminine styles all their lives. So, when a chance encounter occurs in which a man has his first opportunity to feel what it’s like to wear soft fabrics and pretty colors, something may be triggered deep down inside of him that feels wonderful. It’s almost liked a hidden part of his psyche wakes up for the first time in his life when he recognizes his feminine side.

#3 - Women’s clothing is sexy, while men’s clothing is… not so much. When a man spends his entire life wearing the standard uniform that men are expected to wear, and then one day he tries on a pair of women’s underwear, a lightbulb goes off in his head. “Wow” would be one word to describe it. And once the cross-dressing ‘bug’ has bitten him, there’s rarely thought of going back to wearing all drab again.

#4 - Something sexual may have happened the first time a man wore women’s clothing. Slipping on a pair of nylon stockings or pantyhose may have been sexually arousing - and he may have pleasured himself to the point of climax. That’s a positive “reward” for cross-dressing, and often the beginning of a lifelong habit.

#5 - Wearing women’s clothing can be very relaxing for a man. A lot of men release the day’s stress while they’re dressed in women’s garments.