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Goofy Print Underwear:
Boxers with red/pink hearts
The Riddler apparently has green question-mark print boxers.
Deadpool is occasionally seen in boxers with his logo (a stylized version of his mask) on them.
He's also occasionally seen in boxers featuring other heroes' logos, including Captain America. One gag featured him upset that his Squirrel Girl Underoos(TM) were improperly washed. That's right, Squirrel Girl. Might explain why she's so vicious towards him.
And to make matters even nuttier, that particular issue happened long before Deadpool even knew that Squirrel Girl even existed. Here at TV Tropes, we like to call this .
foreshadowing His recent adventures take this to a whole new level of horrifying as he has acquired Jean "Marvel Girl" Grey's original costume, complete with tiny yellow panties. An attempt to impress some ladies by stripping down reveals that he wears these when his other clothes are being laundered.
David Qin from also had a pair with teddy bear print. They were a gift.
Strangers in Paradise A comic strip featured the Eighth Doctor jumping through various Doctor Who Magazine Elseworlds. In the one where he was an ordinary human in a relationship with Dr Grace, the one Doctor-ish touch was the question-mark print boxers.
In one Spider-Man story ("Perceptions", where Wolverine guest-starred), Peter wore Felix the Cat boxers. ◊ (Artist Todd McFarlaine often slipped Felix into the background art, and in this story, where a character actually commented on it, he was scripting the story as well.)
In one story where Superman Mr Mxyzptlk had taken over Metropolis and Superman and Lex Luthor were in an Enemy Mine situation, they attempt to infiltrate "Mxcorp" disguised as guards. Mxy waves a hand to remove their uniforms leaving them in boxers. Supes were blue with an S-shield pattern, and Lex had green with "L"s. (It seems likely Mxy added this touch For the Lulz.)
The cover of the Free Comic Book Day 2014 issue is a parody of the famous image from Two Thousand AD #50 ("Spider-Man No More!") in which Pete in street clothes walks away from a bin with his Spidey-suit in it. On this cover Spider-Man Judge Dredd is walking away from a re-syk bin containing his Judge uniform, while wearing nothing except boxers printed with his badge.
Other men's underwear
Childish women's underwear