I think everyone has an inner gay man.
Mine occasionally tells me that wearing a pink silk shirt (hand-me-down from my grandma) is a good idea.
Or that I'd look real cute if I wore my pirate bandanna as a neckerchief.
(That one actually wasn't so bad, but silk shirts don't breathe. Not fun.)

Being a high school kid with no job and almost no money, my style needs are really different from what yours are, since I don't have to deal with professional wear and stuff yet. Though I did have to get some blazers and slacks for Model UN.

I think UGG boots are an excuse for the stupid girls at my school to wear miniskirts and shorts longer into the winter. Really.

I really don't have any problem with leggings, provided you wear something long over the leggings, like a skirt or a dress or something that covers your thighs. I've seen people make them look rather nice.
And I've got a pretty cute babydoll dress. But I've got a pretty thin waist, and decent legs. It's just the middle part that's the problem -- tummy, thighs -- so it fits well on top and then the bottom flares out just enough so that it hides my problem areas. But I've definitely seen people where it doesn't work. I definitely think people need to figure out more of what works for them.
Like back when the bubble dresses were super-popular. Ugh. Disgusting.