Everyone has a need for personal confirmation of their values: especially HBs and super HBs (unless they're super high self-esteem: in this case a direct neg works). However, in most situations, bringing up a topic about which a girl is clearly proud will mean she'll fish for compliments. In this situation, not providing her with one, or with a back-handed compliment will not only allow you to be cocky-funny, but will allow you to tease her for fishing for compliments. You're not negging, you're pushing her into an alleyway in which she should expect to be negged, and into a topic she brought up (which girls love). By PUSHING her into a NEG, she can't be offrended, and will generally feel sheepish for actively indirectly requesting a compliment in my experience. To each their own.

Example to a girl wearing a leather skirt:

You>>Leather? I usually like leather. Good call.
Her>>Usually? What about my skirt?
You>>It's alright I guess. I'd give it a 4/10. Not as good as my shoes.
Her>>Oh shut up. Why are your shoes so good?
* If she's offended immediately - you can call her on fishing for
compliments. Otherwise, continue the teasing until you can call
her on being arrogant. If you choose to here, you can talk about
your sense of style for a brief validation (if you have good style),
but keep the focus on her fault momentarily.

A word of warning: do not do this on someone actually NOT wearing a nice set of shoes, etc. I did it once at a strip club and the girl was actually embarassed - she had borrowed her friends shoes that did not fit and said they made her self-conscious on stage.

Have fun!