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?
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