Thor and Thrym
Thor, the god of thunder, was one of the earliest males to try out female clothing. He was not very keen on doing it, but was persuaded by his brother Loki who was a champion of unexpected things. (Loki also defied gender stereotypes by giving birth.) In this instance, the gods were in a bad spot because the giant Thrym had stolen Thor’s hammer and used it to blackmail the gods into agreeing that the goddess Freya would become Thrym’s wife. This demand was unacceptable to the gods, of course, but they needed the hammer and decided to deceive Thrym: Thor dressed as Freya and Loki dressed as her maid – together they presented themselves at Thrym’s home. The disguise must have been quite convincing and Thrym was delighted all around. He even laid the precious hammer down on his bride’s lap. Sadly for him, it was the last thing he did.
Author: GW
Sources:
https://en.wikipedia.org/wiki/%C3%9Erymr
Mudrak, Edmund: Nordische Götter- und Heldensagen; Ensslin im Arena Verlag, 2003.