Moe over on tumblr (mopsthefloors dot tumblr dot com) has some amazing headcanons about genderqueer Usopp (which you can see on her tag "op-liveblogging"). I've finally cobbled together a fic that uses a few of her great ideas. Go look at her headcanons, they're fantastic.
Overalls were nice because they were pretty genderless. Girls wore overalls. Boys wore overalls. Girls usually wore shirts with their overalls, but Usopp couldn't really be bothered. Just because sometimes he felt more she than he didn't mean he had to be meticulous about his appearance- that had never been his style. He was meticulous about lots of things- about making gadgets, about shooting accurately, about staying alive… not about clothes.
It was better not to think too hard about what he was wearing.
...
Nami wasn't the first to dress him up. He'd played around in his mother's too-big dresses when he was little, but everyone did that, right? And maybe he'd worn them a few times when he wasn't so little, but that was just in her memory.
Nami was the first to make him feel like he wanted this.
It was before the Grand Line, even. Sometime around Logue Town, probably. Sanji was buying food in port and Luffy had tagged along after him and Zoro had tagged along after Luffy. Nami and Usopp had stayed behind to watch the ship.
Well, Nami was watching her newest purchases more than the ship.
She was parading around the deck, showing Usopp her hundredth newest outfit when she stopped suddenly. She squinted at Usopp, poked his skinny sides and squeezed his noodly arms.
"Come with me," she said. Usopp didn't have a chance to remind her that they were both supposed to be watching for enemies. She grabbed him by the arm and dragged him into her room.
She pointed him to a pile of skirts and dresses and panties and watched with her hands on her hips and a smirk on her lips as Usopp dressed himself with less complaint than she'd been expecting.
"You look good," she'd told him, as he'd stood there in a polka-dotted sundress that just reached his knees, black lace panties and a bra that didn't fit his chest right underneath. He still didn't want to admit how happy that had made him.
It became a sort of game, a habit. Maybe the others didn't know- he liked to think they didn't, but with this crew you never knew.
Robin knew as soon as she joined the crew. Robin knew everything. She joined the fun, dressing Usopp in her own image, tight black leather and lace.
He enjoyed being their dress-up doll more than his pride would let him admit.
3D2Y
Usopp walked into the kitchen in nothing but a sundress, arms and feet bare, and Sanji nearly swallowed his cigarette.
"What the hell are you wearing, shitty sharpshooter?" Sanji shouted, gripping the edge of the counter with white knuckles.
Usopp froze. Two years was a long time; long enough to forget that he hadn't always paraded around proudly in whatever he liked.
"Clothes," Usopp squeaked. He coughed, squared his shoulders and repeated more bravely, "My clothes."
"You're wearing a dress," Sanji moaned. If Usopp hadn't known any better he would have said Sanji sounded almost scared.
"Yes," Usopp said. "Heracles gave it to me."
Heracles, who hadn't minded when Usopp had tentatively replaced his stretched-out clothes with a skirt, who'd even worn a dress sometimes, too, and had told Usopp that the bravest men were the ones who didn't worry about being men at all.
"What kind of sick person did you train with?" Sanji shouted.
Usopp's heart sank. A sick feeling built up in the pit of his stomach, a sickness he hadn't felt in two years, a sickness he'd forgotten he was used to living with.
"Heracles wasn't sick," Usopp defended, but his shoulders were slumped in a way he'd promised himself they would never be again.
"Did we all train with sick freaks?" Sanji huffed, ignoring Usopp.
"What? Who did you train with?"
"Shitty shitting… shit…" Sanji grumbled. He lit a second cigarette and put it to his lips before realizing he was already smoking. He considered the second cigarette for a moment, then put them both in his mouth and stormed out of the room.
Usopp's knees suddenly gave out and he found himself collapsing onto the dinning room bench. He looked down at his dress; it was a very nice dress, a little longer than knee-length, a little tight across his broad chest but ruffled at the bottom, covered in a flower pattern that suited Bowin Island perfectly. Come to think of it, Usopp wasn't entirely sure where Heracles found clothes on that isolated island, but Usopp had left the island with more clothes than he'd ever owned before. Heracles was a fan of costumes and flamboyance, capes and masks and armours, and Usopp couldn't complain.
The door to the kitchen was suddenly slammed open and Usopp leapt to his feet.
"Where's cook-bro?" Franky asked, filling up half the room with his wide shoulders and even larger personality.
Usopp wanted to dive under the table, wanted to hide until Franky left and he could sneak out and change back into something that he was supposed to wear; dresses and skirts were only for nights when Nami decided she wanted a dress-up doll, and Usopp couldn't believe he'd forgotten that.
"Hey, nice dress, bro," Franky said. One massive red hand came down on Usopp's shoulder and Usopp only flinched a bit.
"Nice?"
"Yeah, longnose-bro. Would be nicer with some stockings, though. Fishnet, I think they're called. Good for a pirate."
Usopp almost choked on his own spit. If Sanji's reaction had shocked him back to his senses, Franky's had just thrown him for a loop he hadn't been ready for.
"Fishnet stockings?" he squeaked. He coughed, because his voice was really getting out of hand, but Franky interrupted him before he could repeat himself.
"Fishnet stockings are superrr! My family back on Water 7 had the finest collection of fishnet stockings on the island."
A vague memory of Franky's family sprang to Usopp's mind. He'd entirely forgotten the strange men with their fishnet stockings and starry body suits, because Water 7 was something he'd worked hard to forget in its entirety.
"I wore some myself a few times," Franky mused. "Too much like pants though. I'll stick to my super sea panties."
Usopp watched as Franky wandered over to the fridge, unlocked the locks he'd installed for Sanji and took out a bottle of cola.
Usopp squared his shoulders, put one foot on the bench and crossed his arms proudly across his chest.
"Well, yes, this dress might look nice with stockings, but the Great Captain Usopp can make anything look fantastic!"
Franky laughed and tipped his foaming bottle at Usopp.
"But the new and improved Battle Franky 37 can make anything look superrr!" he said, and whipped a ruffled pink shirt out of thin air, which was a talent Franky and Heracles seemed to share.
Franky threw the shirt on and posed dramatically, slopping soda onto the counter. Usopp grinned hugely and jumped onto the table, pointing at his chest with his thumb.
"No! The Great Captain Usopp is the most fashionable!"
Franky leapt over the counter and crashed to the floor next to the table. He reached up and grabbed Usopp around the waist, throwing him over his shoulder.
"Hey!" Usopp shouted.
Franky sat Usopp down on the counter, then scratched his chin, giving Usopp a once-over.
"Alright," he said. "I'm feeling generous this week. The Great Captain Usopp is the most super!"
Usopp laughed and moved to jump off the counter, but one of Franky's huge red hands grabbed him before he could. Franky pulled Usopp close to him and kissed him, tasting of cola and metal and everything Franky. He pulled his head back and nodded.
"Definitely the most super."