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The first time Oswald tries on lipstick he sneaks one from his mother’s vanity in her room. It’s bright pink and the only reason he chose it was because of the shiny, rose gold packaging.
He ran to the bathroom and, stood on a small stool, he applies as neatly as an 8 year old could. He loves it. He smiles at himself in the mirror, not even paying attention how some of it has gotten on his teeth.
He feels pretty .
He’s 13 when he starts wearing eyeliner. A cheap, black pencil he lifts from the convenient store underneath his apartment building. He stuffs it in his backpack along with a tube of clear lipgloss and waits until he’s at school to apply them.
His mother caught him wearing them once, and she warned him that it would only cause him trouble. She had no issue with how her son wanted to express himself, but she worried for his well being. She knew how cruel people could be.
Oswald doesn’t care. He loves the way his eyes look lined in black. Those green irises sparkling surrounded in darkness. He smudges the liner slightly, and sweeps on the clear gloss, checking himself out in the dirty bathroom mirror in the boy’s bathroom.
He smacks his lips together and smiles at his reflection.
He still feels pretty. Even if the boys who come in and catch him confiscate his pencil and gloss and flush them down the toilet.
He slashes the tires on their bikes before he heads home after school.
He’s out of high school when he attempts a full face of makeup. Nothing drastic, just some powder foundation, heavier liner and one color shadow, and a bold lip color.
His mother still worries, tells him about all the stories she hears, about boys who go missing, never come home.
He reassures her he can take care of himself. Doesn’t tell her about the switchblade he carries. Or how he’s had to use it a few times already.
He knows. He knows dressing how he does, acting like he does, is bound to get him some attention. Good, bad, and other.
He’s not weak. He handles himself and anyone who wants to come and try to lay a hand on him.
So he walks out of his house with his perfectly painted face held high, daring anyone to mess with him.
Oswald Cobblepot does not back down from a fight, and he will not be placed in a box and let the world tell him who he can and cannot be, who he can and cannot love, and what he can and cannot wear.
He feels pretty, and no one can take that from him.
He stops wearing makeup when he gets picked up by Fish Mooney. He still sports a bit of black eyeliner, but he ditches the foundation and lipstick. It’s the first time he learns that he has to compromise sometimes.
Fish is a big time player, one of Falcone’s own. She runs with a tough crowd. Fish tells him off the bat that she doesn’t judge him for wearing makeup, that she couldn't care less so long as he stays glued to her hip and doesn’t let her hair get wet.
But Oswald takes one look at her men and knows he has to choose between lipstick or having very unpleasant confrontations with those thugs, chalk full of machismo and a lacking self control.
He leaves his makeup at home, but still lines his eyes.
He still feels pretty, even after Fish beats his face in for backstabbing her.
He reopens his club and the place fills to the brim every night with Gotham socialites, rambunctious youth with too much of their parent’s money, and Oswald has never been happier.
So much that he starts wearing makeup again. He runs the underground, people respect him, they fear him. He does what he wants and looks how he wants. If someone doesn’t like it, well, Oswald had a dagger fitted into his cane for a reason.
He does it right this time. Gets himself proper foundation, eye makeup, lipsticks. He buys glitter .
But when he runs for mayor, he falters. He’s only ever had to stop wearing makeup once and that was for safety. This time, his identity is being challenged, and he does not like that. He’s going to be a politician, and politician’s don’t wear glitter on their eyes.
“According to whom?” Ed asks one morning as they’re having breakfast.
Oswald pauses, holding the newspaper up but keeping his eyes on Ed.
“Ed, I can’t go out there wearing glitter on my eyelids,” Oswald scoffs.
“Well, obviously not glitter,” Ed says. “But who says you have to stop wearing makeup all together?”
Oswald eyes him, skeptical and wary.
“You already have to wear makeup to be on camera,” Ed continues. “What’s the harm in a little eyeliner and mascara? FIll in your eyebrows like you always do.”
Oswald stares at Ed, mouth open slightly. Not that Ed has ever given Oswald a reason to not trust him, but this is new. He’s never had anyone actively encourage him to wear makeup. None of this Wear what you want, I don’t care , or Wear it, but be careful .
No, Ed is actually encouraging him.
“I’ve seen you at the club, decked out in all those colors,” Ed comments. “You seem so comfortable. And you look amazing.”
Oswald can feel his face flush slightly at Ed’s comment. It feels nice to have the man you may or may not have had eyes for acknowledge your appearance.
“But whatever you choose to do,” Ed says, getting up to clear their plates, “I will support you and stand by you.”
He smiles and walks to the kitchen.
Oswald sports a bit of eyeliner, some lipgloss, and fills his eyebrows in subtly.
He wins the election, becomes Gotham’s new hope. He has Ed by his side.
And he still feels pretty.