Hello There,
Although his adventures may not be as grandiose or exciting as Superman's, Jimmy Olsen still has quite the impressive back catalogue of adventures. But this is a crossdressing themed blog after all, so today we're going to highlight the stories which feature Jimmy crossdressing. There's quite a few to go through, so lets get started! I'm including all the relevant comic panels so we can go through all of Jimmy's crossdressing escapades together! Be sure to click the images to make the comic panels easier to read!
Leslie Lowe, Girl Reporter!
Jimmy Olsen #67, March 1963
In this issue from his self titled series: after quitting due to a failed ultimatum looking for a raise, Jimmy enters the job market to discover that the only positions he can find are for girls. He disguises himself as "Leslie Lowe" and returns to his previous employer The Daily Planet, planning to screw things up so badly that Perry White will jump at the chance to hire him back as Jimmy. Of course things don't go as Jimmy planned!
Jimmy Olsen's Female Fan!
Jimmy Olsen #84, April 1965
Who knew Jimmy Olsen had a fan club? I guess the Superman fan club wasn't taking any new members, or Wonder Woman's, or Batman's. Why exactly is there a Jimmy Olsen fan club? Anyway, after the current president of the club moves away, a contest is held to replace him. But in the meantime, the members are faced with the most alien and terrifying thing they've ever encountered, a girl! But what is the link between this new female fan and Jimmy Olsen?! I'll give you three guesses LOL.
Miss Jimmy Olsen!
Jimmy Olsen #95, September 1966
In perhaps his most famous crossdressing escapade, Jimmy goes undercover as a showgirl to track down some stolen jewels. Unfortunately, his disguise is too good, as "Julie" catches the eye of one of the gangsters, causing some trouble for ole Jimmy, or should I say Julie?
The Day They Unmasked Mr. Action
Jimmy Olsen #159, August 1973
On the run from the police for allegedly selling his secrets of being a master of disguise to criminals, Jimmy Olsen crossdresses to avoid detection from the cops.
All Star Superman #4, July 2006
Jimmy briefly demonstrated his affinity for crossdressing at the beginning of issue 4, of the famous All Star Superman series. Here Jimmy scoffs off the idea of being the worst dressed in metropolis, because, well, just look at him, he's Jimmy Olsen!
My Brother... My Bombshell...
Superman's Pal Jimmy Olsen #10, May 2020
After faking his death to uncover a secret plot, Jimmy Olsen confronts his brother about a role he may have played in putting a hit out on Jimmy. Jimmy does this at his own funeral! Of course Jimmy couldn't just walk in (being dead and all), so he infiltrates his funeral by dressing as a stunning bombshell of a babe! He then passes on a godfather-esque message to his brother, revealing Jimmy knows all about his role in putting a hit on Jimmy.
A Whole Universe.....For Crossdressing
Superman's Pal Jimmy Olsen #11, June 2020
Here having tied up loose ends following his fake death, Jimmy Olsen speaks with his ex-wife about what was next for him. Well Jimmy fantasizes about all of the different Super Hero adventures he could go on, one of which shows him dressed as Wonder Woman. I must say, he pulls of the red white and blue well!
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Well there you have it, Jimmy Olsen's crossdressing through out the decades! Jimmy has has a long history in comics so I'm sure there's some crossdressing adventures I've missed. But regardless of that, even what's pictured here is quite the library of crossdressing adventures. Which of Jimmy crossdressing looks were your personal favorites? Mine were the green dress he wore as Leslie Lowe, Girl Reporter, and of course his red bombshell look in Superman's Pal Jimmy Olsen #10. With the recent popularity of James Gunn's Superman movie (2025), there's sure to be more Superman, and hopefully Jimmy Olsen comics on the way!