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Comments

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xylem

I know this is like 4 years before that silly meme became a thing, but I immediately thought this was something like “soygirl waif vs chad waifu” or something like that.
Pony Rocker

My feelings exactly! But to be fair about those who headcanonize Fluttershy in flowing skirts/dresses, they probably just envision her as a Snow White archetype who befriends the critters and no heavy work.
Background Pony #7F15
She definitely looks like the one on the right when working. “Cleans up” to the one on the left surprising all (showers are a thing, and keep in mind who makes the clothing custom when the Mane Six need to go to anything fancy!)
 
Would keep the tan, of course. Though I prefer her a bit caramel-colored from birth.
Japanese Teeth
Non-Fungible Trixie -
Wallet After Summer Sale -
The End wasn't The End - Found a new home after the great exodus of 2012

Clock. Is. Ticking.
My own headcanon for her is probably somewhere between the two; the tanned-ness and practical clothing makes sense, but I don’t think she’s particularly muscular (toned, yes), and I think that the the boots and gloves are a bit much. She does care for animals, but 90% of the time, it seems to be more of a “gives them food/water and shelter” type of thing rather than the park ranger/farmhand thing that this shows. She probably ‘‘does’’ deliver the occasional baby or something, but I don’t think it’s an everyday occurrence for her. It’s not like she’s a rural veterinarian or anything; she’s not constantly wading around in sties and performing surgery on farm animals.
Background Pony #AFA5
I agree with the arguments of the right. But I’d probably try to find a middle group between her sweet femininity and the tough practical nature of her jobs.
 
To be honest, I’ve always pictured Fluttershy wearing something similar to what the EG version of applejack wears. Boots (rubber ones) with a tough skirt or shorts of some sort, with a turtle neck sweater and vest.
Background Pony #AAA8
@Krek
 
But she was only the ideal model for Photo Finish because of her shyness, if anything she isn’t that model-like because Photo Finish ignored her until she acted shy.
GreyDaze
Non-Fungible Trixie -
Wallet After Summer Sale -

@Krek  
Being a physical Laborer and caretaker shouldn’t automatically rule out being fit for modeling either, which is mostly about body proportion.
MooseMcgillycuddy

I can dig this.
 
If you want to incorporate all of her character ideals, she’d be closer to what fanon Applejack is, just quieter and more on the glamor side.
Krek
The End wasn't The End - Found a new home after the great exodus of 2012

What did Photo Finish see in Fluttershy that made her a good model for a modelling career?
 
I agree that a humanized Fluttershy should incorporate more of her animal caretaker element in her design, but we can’t ignore the fact she was the ideal model for Photo Finish.
 
I like to imagine Fluttershy trying to hide or be ashamed of something about herself (perhaps above-average breast size), since it can get her a lot of unwanted attention (as seen in “GiNYC”).
gasmaskangel
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Artist -
Since the Beginning  -

I think I know why the left humanization is the most common one. Fluttershy in canon has a sort of Disney Princess vibe going on that makes it stick. Yes she is shown caring for the adorable woodland critters, but in a very hygienic, sanitized way like Snow White singing while the animals do the house work.
 
Shy herself is shown as a very soft, non physical character, not really as someone who gets her hooves dirty.
 
Contrast with Applejack where while the farm work is still shown in an idealized way it is still shown as hard work.
Orphaned Account
Not a Llama - Happy April Fools Day!

I never paid any mind to how humanized Fluttershy would look like, but I know for a fact that I never saw har as having a long dress as her usual wear or having the behavior you mentioned about it. But yes, your interpretation makes one hell of a lot of sense.
 
Faved for reference.