It started out as any normal, typical school day.
The Cutie Mark Crusaders were plotting whose life they were going to gatecrash next under the cunning pretence of helping them understand their true destiny. After all, those funky shields weren't just for show.
Snips and Snails had ill-advisedly decided the stick of chalk nearby looked rather tasty, and generously snapped it in half to share as an early morning snack. Needless to say, the dim-witted colts now had very dry mouths and hilariously miscoloured tongues.
Lastly, Miss Cheerilee had a full thermos of extra-strong coffee under her desk to deal with the endurance test that lay ahead. At least she claimed it was coffee. Hmm.
So all in all, things were proceeding exactly as you'd expect in good ol' Ponyville Elementary...
But, as many of the residents in this neck of the woods would tell you through harsh, bitter experience, the serene atmosphere can flip in an instant. Why, one minute you could be pondering whether to purchase cucumbers or tomatoes to go with your special salad from the local market, the next might find you having your very essence sucked out by an escaped Tartarus centaur and his chuckling draconequus lackey.
Still, despite the continual mishaps, misadventures and misery the citizens had to deal with, at least it was never monotonous. After all, hugs and kisses and smiles and rainbows are great, but everypony feels like a bit of tension every now and then. And if there's one thing the Ponyville populace quickly realised after six and a half years of drama, ever since Twilight Sparkle's fateful arrival in a hot air balloon that sunny afternoon, it's that they'd received more than their fair share of excitement.
In fact, somepony could almost suggest she bought the tumult with her to that formerly quiet town... but it just wasn't the done thing to accuse the now-princess of such a thing, and such deviant voices were soon crushed by her countless admirers. Long live the establishment!
Regardless, whatever major crisis the youngest equine inhabitants of this backwater hamlet had to tolerate in it's recent checkered history, nothing, nothing at all could prepare them for what they were about to witness.
An Ursa Minor chugging down a huge bottle of cow's milk? Bear-ly!
A pink party pony playing a pretty polka to pacify a platoon of parasprites? Pff!
Discovering local daredevil and all-round toughie Rainbow Dash regularly indulged in a bit of R&R at the spa, including full mud pack and hooficure treatment?
...Okay, so maybe that ground-breaking event cut what was about to 'go down' slightly close in the OMC stakes (Oh My Celestia), but most would say that today's startling revelation still won by a muzzle. Shall we stop rambling, and find out what it is?
Diamond Tiara... wandering into class... as bold as brass... wearing a massive cowboy hat... what'd think about that?! Please try not to faint, both at the unbelievable sight, and the terrible use of poetry.
There had to be at least five, no ten gallons worth of floppy headgear up there, yet she drifted through the hushed classroom as if nothing whatsoever was amiss.
The only words she uttered as she deposited her pastel posterior next to an open-mouthed Silver Spoon was a brief greeting to Miss Cheerilee, who was suddenly gulping down 'coffee' like a fish inhales water.
And no, before you ask, it wasn't "Howdy". Just because she resembles a Western star now, doesn't mean she effected all of their mannerisms. Silly.
Anyway, even though everypony present was as shocked as an electric eel caught on a live wire, the designated lesson schedule still had to proceed. As it was, hardly of the youngsters there could concentrate on the Glorious History Of Canterlot for copping a snoop at the newly-attired pink filly behind or in front of them, although she seemed blithely aware of the interest generated in her appearance.
Indeed, Diamond Tiara was the only one who'd finished the test before the bell rang for recess, everypony else being too busy chattering, murmuring or speculating as to the origin of this bizarre fashion choice. Even a stray paper airplane thrown by one of the more disruptive class members which nestled safely in her brim failed to distract her at all.
By the time she'd left to enjoy her break, most ponies were still present in their seats, half-filled out worksheets in front of them with mostly wrong and/or illegible answers. The faculty's sole focus seemed to be the oversized hat now sported by their wealthy classmate, and they wouldn't rest until they discovered the assuredly fascinating story behind it.
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"You're her best friend... you ask her!" Scootaloo demanded of a certain grey filly.
"I can't. It'll be too weird." Silver Spoon was not one for asking awkward questions.
"I ain't ever seen anythin' like that before. Even ma cousins who live right down in Appaloosa wouldn't wear somethin' that crazy gigantic..." Now Apple Bloom was getting in on the conversation.
"Where did she even get it from?! We certainly don't sell stuff like that in the boutique, and that's the only place in town I've ever seen her mother shop for clothes." Sweetie Belle pondered, with that deep-in-thought expression that'd almost become her trademark.
" 'Er family are loaded, right? She probs ordered it from abroad, though why go to all the trouble for that, I dunno..." Rumble voiced his opinion in his usual brusque way.
"I always thought that tiara looked a little tacky, but nothing like as obnoxious as what she's got on now." Button Mash briefly deigned to glance up from his hoofheld Chronic The Hodgeheg game to mumble a syllable or two.
"Hey guys, don't be so rude. I happen to think she looks pretty dapper..." Pipsqueak dared to go against the grain, albeit with a slight blush.
"Well, you would say that, 'lovercolt'. If she came to school smelling like Snips, you'd still be head-over-hooves for her." First Base sneered at the patchy class president with a crush.
"Hey, I resemble that remark!" Snips objected whinily, as he whipped his tail around to disperse a nearby gathering swarm of flies.
"Yeah, what he said! Uh... what we talking about again?!" Snails tried his best to produce a meaningful thought, but only succeeded in overheating his brain.
"Diamond Tiara's tiara, dolt-colt. Or rather, the lack of it. What are we supposed to call her now, 'Diamond Stetson', or something?" Sunny Daze shrugged her shoulders, along with everypony else.
At this point though, Featherweight interrupted the general air of confusion by rapidly gesticulating to the hoofball court, where the main topic of discussion herself was shouting at them. "Hey, are we going to have any fun this recess, or what?!"
Still unsure what to make of the new-look student, the best the rest of her fellow pupils could muster was a feeble wave accompanied with a forced grin, before they resumed their secret deliberations.
Mouth agape upon seeing their rejection, Diamond nearly threw her huge headwear on the floor in pure frustration, but then thought better of it. "Arrgh! I can't stand this!!"
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The rest of the day followed more or less the same repetitive pattern, with much off-the-cuff discussion about precisely why Diamond came to school half-concealing her face, but without any really good answers. The most popular theory seemed to be she that was having her tiara polished or repaired and it would be back on as normal shortly, but if that were the case... why didn't she just show up hat-free that day? Anything would be better than the floppy monstrosity she sported now, surely.
On a couple of occasions, some of the more braver pupils almost plucked up the courage to actually ask the filly herself what the big idea was. They always ended up chickening out mid-sentence though, with memories still fresh of the kind of devastating criticism pre-reform Diamond could level at them. Even though she was much better these days, it would take some time for the rest of the students to overcome their innate fear of her raucous insults.
This sadly, also had the side-effect of making Diamond feel like a social pariah all day long, even at lunchtime when she'd usually be sitting alongside Silver Spoon. Today she was mostly alone, with the only ones not engaged in far-off idle gossip instead of eating being the ever-hungry Truffle, and the wannabe bodybuilder Lily Longstocking, who had to keep up her dedicated regime of eating five dozen eggs every day. After all, she did want to grow up to be roughly the size of a barge.
Eventually, as it does with grinding inevitability every single day, the school bell rang once more to indicate the end of lessons. A rather tipsy Miss Cheerilee's pupils were still picking up their saddlebags and homework as Diamond, unable to cope with any more pointed stares and whispered remarks, grabbed her things first to make a quick exit in front of everypony else.
Out in front to meet her was surprisingly Filthy Rich, enjoying one of his rare days off. After a brief touching father/daughter embrace, the little filly motioned that she wanted to leave the vicinity as quickly as possible, and being such a devoted father, Filthy had little hesitation in adhering to his precious's wish.
On their way to Rich Mansion, quite an illuminating discussion started up. And, here it is, completely unedited:
"Well, was I right my darling?"
"Y-Yes father, I must admit, you were. Nopony asked me any questions about this stupid hat all day long, even though I heard them muttering all about it to themselves."
"Aha, I knew it! What about the rest, Diamond? Did you finish top of your class, like I said you would?"
"...Only because everypony else was so taken in by this horrible thing, it put them off their work enough to give me a chance. Tell me, how did you guess..."
"Well, it just so happens I have a little filly of my own, so I have some insider knowledge of how your generation thinks. Anyway, I'm afraid you lose, and now you have to pay the penalty."
"Oh, Dad! Haven't I already suffered enough, having to embarrass myself in public with this unsightly nuisance flattening my carefully coiffured mane all day long? And the amount of times I bumped into things... please reconsider."
"You remember the terms of our agreement, Diamond: You wore Stinkin' Rich's old hat for an entire schoolday without being asked about it, and ended being the best pupil in your year, so I win. Now, get ready to hear your forfeit."
"U-Uh oh..."
"You must accompany your mother for no less than one afternoon in Manehattan, as she buys you the prissiest, sissiest dresses in the entire city. Later, you will wear one of said dresses for your upcoming birthday party, and I don't want to hear one word of complaint afterwards."
"B-But DDaadd... it was bad enough when she made me attend my cute cenera wearing that stupid frilly thing."
"No 'buts', young filly, other than yours on the train there. I know Mom can be a hoofful, but in case you haven't noticed your annual party is the one time of year she looks forward to spending with all of us. If we do this for her, it'll put her in a good mood for weeks afterwards, and maybe we can start to feel like a family again..."
"What was that last part, Father? I couldn't hear you properly."
"N-Nothing, sweetie. You just start planning for the day out now. Who knows... if it all goes well, I might just be tempted to keep my side of the bargain too, as if I'd lost the bet..."
"You mean, I can invite everypony in class to be at the party?"
"I think we have more than enough room to accommodate them in the mansion, yes."
"I can have a bouncy castle, clowns, a free karaoke machine?"
"I may have to buy some special earplugs for me and your mother for the occasion, but okay."
"...And can I incinerate this stupid hat as part of a big fireworks display, so no pony else has to suffer the humiliation of wearing it ever again?"
"Of cours... hey, wait a second! That wasn't part of the arrangement as you know full well, Diamond. It's a little bulky I agree, but that hat is an ancient Rich family heirloom. Why, before my pappy made his fortune, he was just a common labourer, and he needed something to keep the sun out of his eyes..."
Oh no, not this old chestnut again. Well, if it makes him happy I'll listen to it with fake interest. In the meantime, I have to figure out how I'm going to tell everypony the truth tomorrow about my odd appearance..." Diamond thought ruefully, as she nodded and smiled a lot while the pair marched on together.
Author's Note
Just a random idea I had which I couldn't help but expand upon. I hope you enjoyed. 
