Post-War: DH compliant until epilogue. Hermione Granger is head girl, Theo Nott is head boy. He decides that Hermione needs a makeover, whether she wants one or not is irrelevant. What applies to the best laid plans of mice and men seems to also apply to the best laid plans of wizards and witches.

AN: Yeah Theo is a bit slow on the uptake at first, it's not because he's dumb it's because he's blinded by his own cultural norms and perhaps a bit overeager to do what he thinks is best.

Misunderstanding Pygmalion or Hogwart's Worst Fairytale
"Your ending is damnable; you ought to be shot."-George Bernard Shaw to Sir Herbert Beerbohm Tree

Hermione Granger was asleep on the sofa again. Sometimes the Head Boy, Theodore Nott wondered if she slept more on the sofa than on her bed. She was four months ahead of schedule in just about every class yet she stayed up every night studying until she passed out. He sighed, unsure if he should wake her. They had developed a sort of odd friendship since the beginning of their partnership.
She had defended him against their fellow students who were quick to call him Death Eater scum despite the fact he did not bear the mark. And she had superbly hexed Cormac McLaggen for making comments about Theo's sexuality. "If I were straight I'd propose to you in a heartbeat." He told her.
"No you wouldn't," she replied "My bushy hair would be a turn off for a coiffure connoisseur such as yourself." Her lips turned up in an impish smirk he saw too infrequently. Despite all the celebrity, the adoration, and the galleons that came with being a war heroine she was still quite unhappy. Or perhaps it was because of all these things she wasn't accustomed to Theo began to wonder...
Scheming was practically second nature to him, sure his scheming was seldom malicious but it was scheming. Hermione had been avoiding any and all attention she was receiving from her new status. She didn't give interviews, go to parties, dress up in the fine robes she could afford now. Since her breakup with the Red-Headed Idiot Wonder she had not gone on a single date. Merlin! She was the most eligible witch in England and she wasn't even trying! Sure her hair was a right good mess and she wore clothes that were far too large on her delicate body. But Theo had seen her stepping out of their shower enough times to know she had a beautiful shape underneath all her ill-fit robes. She was lithe and delicate and thanks to his practically force-feeding her curves were filling out in the right places.
A voice in head screamed "Makeover!" A loud shrill voice that reminded him eerily of his great-aunt Hedy. He could make her truly the most eligible witch of the season. Teach her how to dress, to carry herself, to select a proper suitor (Slytherin obviously, he had to have his house's best interests in mind.) and best of all when the Victory Ball came four months from now she would have the greatest revenge on that ginger nuisance Ronald Weasley. He practically cackled as he pictured her hated ex slack jawed forgetting that slag Lavender Brown while Theo's masterpiece glided down the grand staircase of the ministry ballroom. It would be like that play she left lying out once "Pygmalion" the one she told him that the ending in the production was rewritten. What was the original ending? Oh he couldn't remember she kept babbling about some sort of independent woman tosh but he knew that every girl clearly wanted to be a princess, whether she knew it or not. Sure Hermione talked endlessly about her dreams of studying potions and creating new healing draughts but she had to want a glorious white wedding. Obviously Theo would take care of the dress, the floral arrangements, the caterer, the groom too he noted...It would be perfect! What could possibly go wrong?
Sure he had suggested she buy more expensive robes numerous times to be met with arguments like "I don't particularly need them." and "The money could be put to better use elsewere" and when he suggested she fix her hair she replied "I've got more important things to worry about like NEWTS." and when he suggested she needed to show more skin, starting with say, her arms since it was still quite warm she practically ran out of the room. But now he realized he was just taking the wrong approach, he needed to be more sly, more cunning, more Slytherin.

First he'd make a list of everything that needs to get done. No wait! First he'd make a list of all the eligible suitors and then tailor his plan for the best one. He'd make Hermione irresistable to him, whoever he was and then the two of them would ride off on a broom into the sunset together, assuring a deserving housemate his glorious dues AND taking care of Hermione obviously wanted all along (even though she didn't realize it.) And Theo, Theo was going to have a brilliant career as a publicist to the stars when this was all over, maybe an image consultant! And a matchmaker! Oh this was going to be bloody brilliant.

Well as soon as he put her in a proper bed, with proper pillows. God she was going to make the rat's nest on her head even worse! Okay so that was the first step, he decided. Move Hermione, then start outlining his plan for most glorious victory! He may giggled in delight...maybe just a little. Setting the sleeping head girl onto her bed carefully and making note that he'd had to suggest her to get better sheets for her hair the gears in his head already turned in preparation for the next task. Picking Hermione's Slytherin Prince Charming. He'd need to be rich, handsome, and intelligent.
Theo's eyes twinkled with mischief in a way that would recall his school's late headmaster. Prince! He should have seen it sooner. Draco Malfoy! Oh sure he was a broody mess since the war, sulking about since the Ministry froze his family's assets but what better way to be truly reformed (and thereby earn back his galleons twenty years or so early) than marry Miss Muggleborn herself, Hermione Granger. Oh and Theo was sure his favorite little spitfire could pull Draco out of his depressive slump. And Theo would finally get revenge on that wretched Parkinson bitch and her hateful tongue. Ugh! He hated her.
Oh of course Hermione's friends hated Draco and vice versa but really Hermione couldn't truly hate anyone who wasn't totally evil (which Draco wasn't, he was just um...misunderstood Theo was certain.) and Malfoy would get his head from his arse and realize the new improved Hermione Granger would be the perfect next Lady Malfoy. No one was more powerful in the new political climate than HER. And she was smart! He had certainly worked his way through all the empty headed slags of the school and Theo was certain it was very well time for him to meet a proper witch.
Yes his plan was fool-proof Theodore Nott decided. Draco Malfoy had the looks, style, and breeding and Hermione had the social standing (and soon the looks!) that would make them THE perfect power couple. Theo would have to outline a plan to make Hermione, Draco's perfect woman and what girl couldn't resist the charms of a gorgeous emotionally wounded bad-boy? Oh wouldn't that piss off Weasel right and proper! His Great Aunt Hedy like cackle was rising in his throat again.