@ necrobump: ?

I'm sure you would...

I have on many occasions but I won't go into detail lol

I've never fulled dressed up as a woman, but I've worn individual pieces of woman's clothing. Last Halloween, I went as a human skeleton, and I wore a pair of women's tights with bones on them. Really comfortable, too.

As for everyday wear, the only crossdressing I do is wearing a few pairs of women's skinny jeans. It hugs my legs and form fits to them much better than male pants.

Although I would totally wear things like leggings and short shorts in public if it were more socially acceptable. The first would be perfect during the fall and winter, and the latter would be great during the summer. Why do women get all the comfortable fashion?

Boxers > panties

Plus a whole ton of other stuff.
I'd say that in general men's clothing is more comfortable.

This is true. One nice thing about being a guy is being able to throw something on in a hurry and not have anyone in public give a second glance.

However, women just have more options than men. They can wear pants and shorts at any length and most people won't have a problem with that. However, if a man wears shorts a few inches above the knee, he gets the dreaded gay rumors. I have a pair of red jorts from Hot Topic (inb4 "you're an angsty teen") that I roll up above the knee on warm days, and I've gotten quite a few stares and comments.

You're right there. Women can wear pretty much all clothes associated with men, but the other way round is still sadly an issue.

Here in germany all the hipsters are wearing very short shorts lately.
I'm surprised that's frowned upon where you come from.

Although skirts are probably more comfortable than shorts. No pockets, though...

Not in every situation, but I also imagine it to be quite comfy.
I hope skirts for men become acceptable while I'm still young and sexy enough to rock them.