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I just watched Winter Wrap-Up again yesterday and noticed something that still makes me ponder the origin and evolution of Equestrian Ponies. In the first scene of this episode Twilight Sparkle gets herself ready to go out into the cold by putting on boots, a scarf and... a saddle! She does so a bit clumsily, as if she's not even sure how to wear the last item. That scene reminded me of some of Rarity's fashion designs seen in the first episode of the series, designs that also include saddles. Then the dresses worn by some of the fillies at the party in Call of the Cutie also look like saddles. And now in Season Six we have an episode with "saddle" in the title. This evidence (and references to stirrups and bridles in the series) suggests that at some point Ponies were used as mounts and beasts of burden, thus my head canon that Equestria is somehow a Planet of the Apes analogy. Now, before you boo and throw tomatoes at me, think about it logically for a moment. Why are saddles a part of Equestrian fashion? Are they vestiges of the distant past when someone or something was actually riding the Ponies as a mode of transportation? Where are these Pony-riding creatures now? What happened to them? Did they become extinct? Were they overthrown and in turn exiled by the evolving Ponies they had once dominated and domesticated? Is there some dark chapter of Equestria's distant past that has been perhaps intentionally buried for so long that it has been forgotten by the modern Ponies who now don't question the origin and true initial purpose of saddles? Was the alternate dimension where Sunset Shimmer now resides somehow involved? Were the Pony-riders overthrown and banished to this other realm where they built their own unique civilization? We may never know the true answers to these mysteries, but still I can't help but ponder the enigmatic existence of saddles in modern Equestria.

On a deserted beach somewhere on the uninhabited border of Equestria, a lonely Human stands staring in disbelieving horror at the ruins of some ancient Human monument, then shakes his fist at the sky and shouts: "No! They destroyed it all! Damn you Ponies!"

ADDENDUM

In anticipation of skepticism and perhaps even ridicule regarding my Planet of the Ponies head canon, I've prepared the following addendum:

Since my theory focuses on enigmatic Equestrian fashion items, let us go a step further and examine one of the tools we have often seen Rarity use while creating her dresses. It is an oddly-shaped tool with bisected cutting blades and opposite the sharp end of each of these joined, pivoting blades is a loop-shaped handle of sorts. Rarity of course uses her magic to easily manipulate this strangely-shaped cutting implement, but I can't help but wonder how an Earth Pony might attempt to use such a tool. I imagine they would find such a task rather difficult and highly impractical, likely explaining why we have never seen Earth Ponies using these cutting tools. Ponies have no fingers nor opposable thumbs, so I find it highly unlikely that they would have designed such a tool themselves, a tool that only one specific variety of Pony could use easily. Thus this begs the question: if Ponies did not invent this odd cutting tool, then what strange ape-like creatures might have come up with such a design for such a device?

The answer to me seems as plain as the muzzles on your faces My Little Ponies. Equestria has not always been ruled by Ponies, and at some point in the distant past some other, vastly different race of creatures once walked the land. What happened to this ancient race and its civilization? How much of modern Equestria's technology is actually remnants of that lost civilization? The answers to these questions may very well be lost forever in the swirling sands of time.

Further Speculation...

While the following speculation admittedly is not irrefutable proof of another race rulung Equestria before the dawn of Pony civilization, it is in ponderance of the puzzling preoccupation of the Ponies regarding fashion, thus I include it here with my other fashion-related theories.

As I pondered the perplexing puzzles of saddles and Rarity's scissors I was reminded that the very existence of fashion in Equestria is in itself an enigma. While Ponies both male and female obviously find it quite comfortable and normal to be without any clothing whatsoever in public during the course of their daily lives, for some unknown reason they contrarily also believe that for special occasions they must cover themselves with elaborate haberdashery. This belief is so prevalent in Pony society that fashion designers such as Rarity have found fame and fortune in creating appealing garments for Ponies to wear. I can't help but wonder how such a contradictory state came to exist in Pony culture. What events in their history led to their current belief that public nudity is the acceptable norm yet clothing must be worn during certain formal functions? What turning point in their evolution left them with such a paradoxical racial predispotion for casual social nudity but also with an inclination to wear clothing when attending specific social gatherings? I could attempt to weave this mystery into the fabric of my Planet of the Ponies theory by suggesting that perhaps some ancient Pony-riding creatures wore such adornments and that, though they have long since left the realm of Equestria, their practice of clothing themselves somehow lingered with the Ponies they left behind. But I have to admit that such speculation would be grasping at straws, as they say. It seems more plausible that primitive primordial Ponies may have worn costumes during important tribal rituals, perhaps in imitation of the supernatural beings they worshipped or the demons they feared, and as the centuries passed the practice of wearing fancy dress costumes during holidays and important occasions has remained a part of more civilized Pony culture though the rituals of their origins have been long forgotten. Then again, perhaps this does indeed fit in with my head canon of Pony evolution after all. Perhaps the garment-wearing beings the Ponies once paid such homages to were also the ones who once put the saddles on the Ponies. Perhaps Pony clothing in itself is yet another vestige of the ancient society of said beings that has been passed down through centuries of Pony generations though no Pony living today remembers the reasons for such customs or the origins of such costumes. The natives of the strange realm to which Sunset Shimmer and the Sirens known as The Dazzlings were once banished all wear clothing at all times as far as we have seen. Perhaps this is further evidence that the denizens of that dimension are indeed the descendants of the ancient race that once inhabited Equestria with the Ponies.

In a scene during a seemingly innocent music video, clothed Human Applejack sits on a fence while playing her guitar and singing. She is joined by clothed Human Sunset Shimmer, sitting upon the saddled back of a bridled equine. Though once a Pony citizen of Equestria, smiling Sunset now appears to be quite comfortable using the horse as a means of transportation. With a smile, Applejack feeds an apple to the domesticated beast of burden.

And thus, like the proverbial rabbit hole, the mystery grows deeper still...