Scrabbleman
Duck - He literally asked for this
Wallet After Summer Sale -
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Artist -
Birthday Cake - Celebrated MLP's 7th birthday
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
The End wasn't The End - Found a new home after the great exodus of 2012

[screams in German]
@xylem  
I too have fallen for it.
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.
Background Pony #3E31
WHOA
 
THAT’S A WAIFU
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.
Invisifat

Fucking GORGEOUS.
Brokedownandmadeone
Pixel Perfection - I still call her Lightning Bolt
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Non-Fungible Trixie -
Preenhub - We all know what you were up to this evening~
My Little Pony - 1992 Edition
Artistic Detective - For awesome dedication to sleuthing out and maintaining artist tags and links
Notoriously Divine Tagger - Consistently uploads images above and beyond the minimum tag requirements. And/or additionally, bringing over the original description from the source if the image has one. Does NOT apply to the uploader adding several to a dozen tags after originally uploading with minimum to bare tagging.
Cool Crow - "Caw!" An awesome tagger
Wallet After Summer Sale -
Equality - In our state, we're all equal here!

BigThirsty ponybooru.org
Huh. Makes sense.
GreyDaze
Non-Fungible Trixie -
Wallet After Summer Sale -

@Background Pony #B03F  
I imagine the same for all Pegasi, since they’re greek
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.
Osquade

I love this to the bottom of my heart and its grounded point of view that I also share.
 
tis Artist needs praise!
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”).
Deserter
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
The End wasn't The End - Found a new home after the great exodus of 2012

This cykas my blyats
Well, people usually don’t wear their work clothes outside of work.
Orphaned Account
Not a Llama - Happy April Fools Day!

@punksweet  
Sweaters, jeans and sneakers.
punksweet
Artist -

Sweaters, people love to put human Fluttershy in sweaters.
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.
Foric
The End wasn't The End - Found a new home after the great exodus of 2012

Good point
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.
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  -

That’s actually a really good point, and I think I actually prefer the one on the right.
Tumblr Feminism Is A joke
Duck - Derpibooru trolling is a duck
My Little Pony - 1992 Edition

@Hugobertington.Esq  
Been there. You at least drew attention to something good
MushroomCookieBear
A Really Classy Artist - 250+ images under their artist tag
An Artist Who Rocks - 100+ images under their artist tag
Artist -

Professionally Weird
I’ll be honest,the Fluttershy on the right is prettier and cuter than the one on the left. But that’s my opinion.
Noozie
Non-Fungible Trixie -
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!

@Hugobertington.Esq  
Report this as dupe?