very hard to pull off without looking slutty, can only be matched with very specific outfit styles or else you'll just look like a hooker. high class hooker maybe, but still a hooker If you happen to have the outfit that can pull them off though, I say go for it.
Classic red lips:
they look great in the movies, sure. But real life isn't the movies and unless you're going out to a ball or something and are dressed for the occasion, they, also, will only make you look like a hooker.
The blazer is cool. I like it a lot.
Patterned leggings are hideous. One thing that bugs me is when people wear stuff that looks like it should be undergarments as outerwear, and this is one of those instances.