Men wearings womens clothing, what are your thoughts on this?

I've come across several 'cross dressing' questions by men and a few women on here. So I've decided to I'm going try expand the region, but lower the bar.

Some crossdressers (not all) are often sloppy, unconvincing, clad in hooker-esque outfits and are almost always fetishes in which the man desires a submissive role.

I would like to decipher the middle ground, because there always is one. I also accept that a woman might be more inclined to agree with the guy if they've known each other for sometime

But what if they didn't assume that typical template, and what if it in no way affected their dominant personality?

For example; the man wears womens clothing, knowing that they fit, are comfortable, and not necessarily feminine. They may or may not have long hair, but the womans clothing is simply a means to expand their real life fashion and styles.

This means they're confident in what they wear outside and typically care less about what others think. It also means they're likely not panty-stealing-to-wear kinkies or dress-wearing drag queens. The clothes could be anywhere from Masculine to Feminine or a mix of both.

The bottom line questions for this are:

'Would you date this kind of man?'

'If the clothing fits, would you share your clothes? Assuming the proportions were a decent match.

'If not, is it something you could get used to over time?'

Remember that this hypothetical assumes that each outfit is stylish and fashionable enough to feel confident in, that the clothes are not fetishised, and that your clothes and his are interchangeable (an entire outfit may not consist of all-girls clothes, but either a small or large portion). Also that the man has soft enough features to pull off such clothes.

I'm allowing Private Opinions too because it allows people to be more honest and be more willing to speak their mind.

I look forward to hearing your thoughts and feelings!

Some random photographs from the internet about this very subject

Men wearings womens clothing, what are your thoughts on this?
Men wearings womens clothing, what are your thoughts on this?
Men wearings womens clothing, what are your thoughts on this?
Men wearings womens clothing, what are your thoughts on this?
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Thank you for your opinions. I will be choosing MHO shortly
Men wearings womens clothing, what are your thoughts on this?
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