One of the most fun stories to tell to any age group, the Þrymskviða tells the story of Thor's hammer Mjöllnir being stolen by the giant Thrym. He asks for the goddess Freya in exchange for the weapon, and she (dis)respectfully declines. Thor decides to take her place and dress up as a bride, with Loki as his maid, and they manage to fool the giant through the entire wedding, until the hammer is returned. Thor almost manages to give himself away by eating too much, and glaring at the giants, but Loki seems to be enjoying himself.
(Of course it was Loki's idea.)
At some point in his career, Herc also got a taste of women's clothing, although not exactly by his own free will. Serving as a slave to Queen (or, according to some other sources, Goddess) Omphale, he spent a year switching roles with the lady - Omphale wore Hercules' lion skin, and the hero wore a woman's dress, doing women's chores around the house. While not voluntary, apparently the change did not leave a scar on his pride - once freed from the one-year contract, he ended up marrying Omphale, and fathering some legendary children.
(Because who wouldn't want to see Brad Pitt in drag?)
In a famous prequel to the whole Troy shebang, Achilles lived disguised as a girl for a while. Since the prophecy said he would die young, his mother tried to keep him away from fighting by dressing him as a girl, and sending him to live with the daughters of the king of Skyros, a tiny island. Achilles lived under the name of Pyrrha (Redhead), until Odysseus found out where he was hiding, and came to recruit him for the war effort. He brought jewelry and gifts for all the girls, and some weapons; then he pretended the island was under attack, and at the sound of the horns Achilles grabbed up a sword and thus gave himself away.
Story also says that while there, he fathered two sons with one of the actual daughters of the king. I am sure the girls didn't mind the dress.
Hugdieterich
I already wrote about this in my post on love stories from the Dietrich Cycle. Hugdieterich, emperor of Constantinople, not only dressed himself as a princess to get close to the love of his life, but even learned womanly arts like embroidery, in order to impress her father. She spent some time at court teaching the girls womanly arts, before giving away who he was (and fathering some heroic sons). Story doesn't tell if he kept his hobby of embroidery later on.
The leader of the legendary Pandava brothers of Indian mythology, the great and mighty hero Arjuna also spent a year in women's clothing (cursed into an eunuch by a woman whose advances he turned down). He took on the name Brihannala, and taught dancing and singing to a princess. He was later (after changing back) offered the hand of the princess, but declined, saying that he saw her as a student and a daughter. Princess ended up marrying his son instead.
Case in point: Wearing feminine clothing does not tarnish your chances at manly immortality.
One question remains: Who wore it best?
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