There’s drawing Fluttershy in Fluttershy-related outfits,

and then there’s drawing Fluttershy in Fluttershy’s relations outfits.

Today regards the latter...

As numerous as the amount of outfits I’ve either seen or drawn Fluttershy in has been, I don’t think this is something I’ve ever seen anyone do.

With the notion I’ve developed that Fluttershy looks great in basically every outfit she wears, it should come as no surprise that she would hypothetically rock "men’s" clothing as well... To that end, there happens to be a very prominent man in Fluttershy’s life that I could conceivably see (under specific circumstances) sharing, wearing and/or specifically baring the fashion of. That man is her notoriously despised [by the fandom] younger brother; Zephyr Breeze.

In Equestria Girls, specifically the ‘Better Together’ episode ‘Overpowered’, Zephyr makes his debut appearance. He wears a "hippie" looking lace-up vest with tassels, as well as a pair of dark blue, slightly baggy pants. He makes some other appearances throughout the series wearing different outfits, but this is basically his casual fit… and incidentally, the fit I have chosen to depict Fluttershy wearing here!

Maybe Zephyr just wanted to have his sister match him for a day or something, who knows? Whatever the narrative behind this image could be, I just thought it'd be interesting to see Fluttershy sporting her brother's fit.

After all, it's not unheard of for siblings to share wardrobes, right? ;)