I was working on a tomboyish Cream yesterday and my friend suggested me to draw femboy Tails as well so I did it :D
I personally think that a feminine Tails would go for something aerodynamic that also would make him look smart so I just went for pleated skirt and tights lololol.

I was going to make him wear a button-up but when I did it he really looked more like a schoolgirl than anything. And he's te teacher, dammit. /j
I couldn't resist adding a ring with a ribbon. I just am obsessed with the Sonic Title Screen being added as an accessory. I just couldn't help myself lolol